2004 ACS NATIONAL AWARD WINNERS | February 9, 2004 Issue - Vol. 82 Issue 6 | Chemical & Engineering News
Volume 82 Issue 6 | pp. 46-63 | Awards
Issue Date: February 9, 2004

2004 ACS NATIONAL AWARD WINNERS

Recipients are honored for contributions of major significance to chemistry
Department: ACS News

Following is the final set of vignettes of recipients of awards administered by the American Chemical Society for 2004. An article on Elias J. Corey, 2004 Priestley Medalist, is scheduled to appear in the March 29 issue of C&EN along with his award address.

Barry M. Trost, winner of the Arthur C. Cope Award, and most other national award winners will be honored at an awards ceremony, which will be held on Tuesday, March 30, in conjunction with the 227th ACS national meeting in Anaheim, Calif. The Arthur C. Cope Scholar awardees will be honored at the 228th ACS national meeting in Philadelphia, Aug. 22­26.

The Cope Award recognizes and encourages excellence in organic chemistry; it consists of a medal, a cash prize of $25,000, and an unrestricted research grant of $150,000 to be assigned by the recipient to any university or research institution. Each Cope Scholar Award consists of $5,000, a certificate, and an unrestricted research grant of $40,000. Arthur C. Cope and Arthur C. Cope Scholar Awards are sponsored by the Arthur C. Cope Fund.

Arthur C. Cope Award


Trost
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Trost

Barry M. Trost's research is like the work of a carpenter who makes his own tools before beginning to build. In his long career as a synthetic organic chemist, Trost has built a reputation as an innovative and creative explorer of new frontiers in both methodology and synthesis. His exacting standards mean that he is also a very careful researcher, not looking just for what works, but for what works the best and most efficiently. He will receive the award for his contributions to organic synthesis in asymmetric catalysis, total synthesis, organometallic chemistry, and complex molecule synthesis.

Trost was born in Philadelphia, in 1941. He earned a B.A. from the University of Pennsylvania in 1962 and a Ph.D. from Massachusetts Institute of Technology only three years later for his studies on the structure and reactivity of enolate anions under his adviser Herbert O. House. During the time of his Ph.D. research, Trost was a National Science Foundation Predoctoral fellow.

In 1965, Trost was made assistant professor of chemistry at the University of Wisconsin. At this early stage in his career he participated in the isolation and structure determination of the cecropia juvenile hormone. The studies suggested that insect growth regulators could control insect pests with less environmental toxicity than traditional pesticides. In use today are S-hydroprene, S-kinoprene, methoprene, and S-methoprene, chemical analogs of the hormones. These juvenile hormone mimics allow the larva to grow and become a pupa, but prevent the pupa from emerging as an adult. Use of these products is not considered harmful to the environment.

In 1972, Trost ventured to the University of Marburg, Germany, to begin the first of a series of international visiting professorships that have spanned his career. He has accepted appointments to universities in Denmark, Germany, France, Spain, Italy, and most recently the University of Cambridge in England.

In the late '60s and '70s, Trost began research on sulfur chemistry and provided new mechanistic insights and synthetic methods including spiroannulation, secoalkylation, geminal alkylation, and cyclopentannulation. He found that sulfur-containing substrates may function as either electrophiles or nucleophiles depending upon their chemical environment. Trost calls them "chemical chameleons" because of this duality.

Stanford colleague Paul A. Wender reports that Trost's "sulfur chemistry alone provides a striking example of his profound impact, with one paper being so frequently cited as to be listed as a Science Citation Classic." The paper is titled "New Synthetic Reactions. Sulfenylations and Dehydrosulfenylations of Esters and Ketones" [J. Am. Chem. Soc., 98, 4887 (1976)]. Trost's "related work has generated new ways of manipulating chemical reactivity that enables new ways of approaching bond formation and synthesis," Wender says.

Trost became a full professor of chemistry at the University of Wisconsin in 1969. He was named the Evan P. & Marion Helfaer Professor of Chemistry in 1976 and chaired the department from 1980 to 1982. In 1982, he was named the Vilas Research Professor of Chemistry.

Trost continued his research on sulfur-based reagents and transition metals such as palladium and, more recently, ruthenium catalysts for organic synthesis. He has zeroed in on the mechanistic nuances of organometallic reactions to understand the possibilities of transition-metal catalysis, which he promotes as "chemists' enzymes" for their novel selectivity (including chemo-, regio-, diastereo-, and enantioselectivity) and efficiency. For example, he developed a palladium-catalyzed Alder-ene reaction that proceeds at 200 °C lower than the noncatalyzed version. He has also focused on enantioselective catalysts by the rational design of "chiral space" and has designed catalysts for asymmetric synthesis of carbonucleosides (used for the treatment of AIDS) and vitamin D analogs used in the treatment of osteoporosis. The concept of rational design of chiral space also led him to design a novel catalysis for an asymmetric direct aldol addition.

A continuing theme of Trost's research has been "atom economy." ACS President Charles P. Casey credits him with "greatly influencing the ways in which organic chemists think about organic synthesis and devise synthetic strategies." The highly selective catalysts that Trost has developed produce complex targets in high yield with a bare minimum of waste. Being particular about extra atoms and side reactions is very important when assessing the commercial feasibility and environmental impact of larger scale reactions.

Trost won the 1998 Presidential Green Chemistry Challenge Award for his concept of atom economy and his group's development of chemical processes to produce widely used intermediate chemical compounds with substantially less waste than those currently used by industry.

Casey notes that Trost is "particularly famous for the development of palladium- catalyzed reactions such as the alkylation of allylic esters. With palladium catalysis, macrocyclizations to eight- and nine-membered rings become more favorable than cyclizations to rings of normal size such as six- and seven-membered rings. The development of trimethylene methane palladium catalytic intermediates provides a cycloaddition route to the increasingly important cyclopentanoids, which possess a broad spectrum of antibiotic and antitumor activity."

In 1987, Trost accepted a professorship at Stanford University. He is currently the Job & Gertrud Tamaki Professor of Humanities & Sciences. From 1996 to 2002, he served as chair of the chemistry department. His research group is currently investigating new opportunities for selectivity with nickel, chromium, molybdenum, ruthenium, iron, and tungsten complexes and bimetallic complexes. With his students he explores unusual oxidation states of metals for new types of reactivity and asymmetric templates that create enantiomerically pure stereogenic molecules.

In addition to his prize-winning green chemistry work, Trost has won many national and international awards for his work. The American Chemical Society has awarded him the ACS Award in Pure Chemistry (1977), the ACS Award for Creative Work in Synthetic Organic Chemistry (1981), the Arthur C. Cope Scholar Award (1989), the Ernest Guenther Award in the Chemistry of Essential Oils & Related Products (1990), the Roger Adams Award (1995), the Herbert C. Brown Award for Creative Research in Synthetic Methods (1999), the New York Section's Nichols Medal (2000), and the ACS Nobel Laureate Signature Award for Graduate Education (2002). Trost was elected a fellow of the American Association for the Advancement of Science in 1977 and elected to the National Academy of Sciences in 1980. In 1992, he was elected a fellow of the American Academy of Arts & Sciences.

Trost is well known to many ACS members because he teaches the popular and long-lived short course "Frontiers in Organic Chemistry." He is currently on the editorial advisory board of the Journal of Organic Chemistry. Hans J. Reich, who taught with Trost at the University of Wisconsin, says, "Barry brings to his other activities in teaching, publishing, and administration the same kind of energy and dedication that he brought to his research activities for which he was awarded the Cope."

He is married to Susan Trost and has two sons, Aaron and Carey.--MELODY VOITH

Arthur C. Cope Scholar Awards


Miller
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Miller

Scott J. Miller, 37-year-old professor of chemistry at Boston College, rarely knows what a research question will lead to. "Essentially none of our projects has played out exactly as we planned," Miller says. But by letting the questions he poses guide the direction of his research, Miller established in the first seven years of independent research an innovative program utilizing peptides as catalysts in asymmetric organic reactions.

"I find that I am drawn to problems where, at first glance, I do not know how to proceed," Miller says. By continuing to work through those problems, he sometimes finds a way. One of his earliest breakthroughs, according to Samuel H. Gellman, a chemistry professor at the University of Wisconsin, Madison, was published in a 1998 communication in the Journal of the American Chemical Society [120, 1629 (1998)]. Miller found that a tripeptide could act as a reaction catalyst for the kinetic resolution, via acylation, of racemic alcohols.

Gellman says that Miller reached beyond his synthetic organic training when he recognized that peptides could be used as scaffolds in catalyst development. "I know the small-peptide conformational literature well, and I would have predicted failure for the experiments that Miller describes in the 1998 JACS paper. I was so surprised by the exciting results that I instantly became a Miller admirer," Gellman says.

The 1998 JACS paper opened the door to many further studies. Miller and others have explored and continue to expand the possibilities for peptide catalysts. In 1999, Miller developed a simple and efficient method for screening for acylation peptide catalysts from a combinatorial library. Because only active peptides release acetic acid, Miller created a fluorescent probe that detected the presence of acetic acid. And in 2001, Miller demonstrated the utility of peptide catalysts by using one capable of catalytic asymmetric phosphorylation in the total synthesis of myo-inositol-1-phosphate, "providing the most efficient synthesis of enantiomerically pure d-myo-inositol-1-phosphate ever reported," Gellman says.

Miller was attracted to chemistry early in his life. "I remember becoming aware of the molecular world as a young student," he says, "and I have been tremendously fortunate to work with inspiring teachers at every stage of my career." Miller earned his bachelor's and Ph.D. in chemistry at Harvard University, where his graduate adviser was David A. Evans. He went on to California Institute of Technology, where he completed a postdoctoral fellowship under Robert H. Grubbs. Since 1996, he has been at Boston College, where he is now a professor of chemistry.

In the past few years, Miller has received a landslide of awards for his creative research. In 2000, he received an Alfred P. Sloan Research Fellowship, a Camille Dreyfus Teacher-Scholar Award, a DuPont Young Professor Award, a GlaxoWellcome Chemistry Scholar Award, and the Eli Lilly Grantee Award. And in 2003, he was chosen to receive the Pfizer Award for Creativity in Organic Chemistry.

Yet Miller considers his most rewarding activity interacting with his students. He tries to stimulate "curiosity-driven research," he says. "My students and I converse primarily in the questions we pose to one another. As such, we strive to challenge each other with critical thinking. Hopefully, it takes us closer to the answers we are looking for."--LOUISA DALTON

Raines
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Raines

Ronald T. Raines's love of chemistry blossomed during the many long afternoons he spent after school as a teenager, honing his chemistry skills with his teammates on the chemistry team at West Essex (N.J.) High School. And after helping his team bring home the state championship during his senior year, "it was a done deal that I would become a chemist," Raines says.

Now a professor of biochemistry and chemistry at the University of Wisconsin, Madison, Raines, 45, has spent more than a decade "skillfully exploiting the tools of chemical synthesis and molecular biology to address penetrating questions about protein structure and function," notes Donald Hilvert, a chemistry professor at the Swiss Federal Institute of Technology, Zurich. "Raines is highly multidisciplinary in his experimental approach to understanding biological phenomena," Hilvert continues. "But his perspective is decidedly that of a chemist."

Early on, Raines brought that chemical perspective to studying the mechanism of the well-known RNA-cleaving enzyme ribonuclease A (RNase). But he's quick to point out that he likes to tackle problems that aren't only interesting from a basic science point of view, but also have useful applications at the end of the day. A case in point: Raines recently used lessons learned from studying this enzyme's mechanism to create a potentially therapeutic "caged" RNase enzyme that becomes active only when cleaved by a protease found in great abundance in cancer cells or RNA viruses. "This Trojan horse strategy shouldn't be so susceptible to resistance mechanisms" that plague other anticancer and antiviral drugs, he says.

Collagen, the most abundant protein in animals, has also intrigued Raines. Collagen derives its stability from its unusual 4(R)-hydroxyproline residues. Using selectively fluorinated proline derivatives, Raines generated superstable collagen. In doing so, he demonstrated that collagen gets its special stability from hydroxyproline's special stereoelectronic properties--not from bridging water molecules between neighboring collagen strands, as many had long thought. Raines thinks that the superstable collagen might eventually find use as a solder for laser-based tissue welding.

Raines is also developing new ligation methods for assembling semisynthetic proteins, a project that began as a collaboration with his wife, colleague, and fellow Cope Scholar, chemistry professor Laura L. Kiessling. Raines's technique ties together two peptides, one with a C-terminal phosphothioester and the other featuring an N-terminal azide moiety. Unlike other peptide ligation methods, Raines's reaction requires no specific amino acids at the ligation junction and leaves no chemical footprints, forming an iminophosphorane intermediate that rearranges to give a nativelike amide bond linkage.

"This reaction represents a significant addition to the arsenal of tools available for synthesizing large proteins chemically," Hilvert says. In a step in that direction, Raines recently showed that his method can be used on a solid support to assemble full-length, fully active RNase enzyme.

Raines earned bachelor's degrees in both chemistry and biology from Massachusetts Institute of Technology in 1980. After receiving his Ph.D. in organic chemistry from Harvard University in 1986, he spent three years as a postdoc at the University of California, San Francisco, before taking a job as an assistant professor at Wisconsin in 1989.

Among his many awards, Raines received the Pfizer Award in Enzyme Chemistry in 1998 and a Guggenheim Fellowship in 2001. He is also a fellow of the American Association for the Advancement of Science.--AMANDA YARNELL

Shi
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Shi

From the time he started college in China, Yian Shi knew he wanted to be a chemist. As he continued his education first in Canada and then in the U.S., his commitment to the discipline grew ever stronger. Now a professor of chemistry at Colorado State University, Fort Collins, Shi is considered by his peers to be one of the most innovative and productive organic chemists practicing anywhere.

"We try to develop new synthetic methods and their applications," Shi says of his research. As an example, he points to his development of a chiral-ketone-catalyzed asymmetric epoxidation of olefins as "potentially useful."

Other chemists are less reticent in their assessment of Shi's pivotal work, first published in 1996. "The Shi epoxidation is already a name reaction that will clearly be written into the textbooks," says Barry M. Trost, professor of chemistry at Stanford University and Shi's Ph.D. research adviser.

Earlier examples of highly enantioselective epoxidations are mostly based on metal catalysts. Shi's approach, however, uses chiral carbohydrate ketones as catalysts. These ketones are transformed during the reaction to dioxiranes that transfer oxygen to the starting alkenes. The scope of the reaction is broad, including trans olefins and trisubstituted olefins that don't work well with other epoxidation procedures.

"This remarkably controllable synthetic transformation has not been observed very often during all the history of organic reactions," notes chemistry professor emeritus Albert I. Meyers, Shi's colleague at Colorado State. "The products obtained are of immense utility (pharmaceuticals in particular), and worldwide interest in this chemistry has resulted in a large number of invitations to speak and reviews to write. It is not very often that we see a young scientist making such a huge impact in his field."

Shi's group is still studying and refining the reaction, making it more practical. It is being used by other researchers and explored for use in industry.

Not just a star in the laboratory, Shi is also recognized as an effective mentor. "His breadth of knowledge, his willingness to share his knowledge, his unassuming manner, and his ability to think clearly also make him a particularly effective teacher," Trost notes.

Shi, 40, obtained a B.S. in chemistry from Nanjing University in 1983. He studied at the Shanghai Institute of Materia Medica before moving to the University of Toronto, where he obtained an M.S. in chemistry in 1987. After completing his Ph.D. at Stanford in 1992, he spent three years as a postdoc at Harvard Medical School with Christopher T. Walsh. He joined the faculty of Colorado State as an assistant professor in 1995.

Shi's many other honors include a Beckman Young Investigator Award, an Eli Lilly Grantee Award, and a Camille<br > Dreyfus Teacher-Scholar Award.--PAMELA ZURER

Wood
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Wood

According to Amos B. Smith III, Yale University professor John L. Wood "does exciting science by undertaking what he does in great depth. He is not fearful of asking questions or probing below the top level."

Wood earned his B.A. in chemistry, summa cum laude, from the University of Colorado, Boulder, in 1985, and his Ph.D. in organic chemistry from the University of Pennsylvania, under Smith, in 1991. The latter half of his undergraduate career was supported through a research assistantship in the laboratory of professor Christopher Shiner, an experience that inspired Wood's eventual pursuit of the Ph.D. After working as an American Cancer Society postdoctoral fellow from 1991 to 1993 with professor Stuart L. Schreiber at Harvard University, Wood joined the Yale faculty as an assistant professor.

At Yale, Wood rose rapidly through the ranks, being promoted to associate professor in 1997 and full professor in 1998. His research has focused on the development of efficient strategies for the synthesis of natural products and the application of total synthesis to questions of biological interest.

Describing Wood's research, University of Pennsylvania professor of chemistry Madeleine M. Joullié says: "Within less than five years of his start at Yale, John established a highly visible synthetic program. This effort has led to three total syntheses, the development of and application of a highly stereoselective tandem Claisen-a-ketol rearrangement, and the extension of the latter technology into the bioorganic area. Particularly notable from this period of John's work are syntheses of (+)- and (­)-syringolides 1 and 2, and of (+)- and (­)-K252a, a close relative of the potent protein kinase inhibitor (+)-staurosporine."

Smith says, "Equally impressive are John's mechanistic studies relating to the rhodium carbenoid chemistry discovered and developed during the (+)-staurosporine venture. This work opens an entirely new approach for the enantioselective construction of complex a-hydroxy carbonyl derivatives."

In recent years, Wood's research program has continued to focus almost entirely on the synthesis of natural products, with a particular emphasis on bridged polycycles. "Compounds in this class often have structures containing densely packed arrays of various functional groups, heteroatoms, and stereogenic centers, all of which continue to present daunting challenges to the synthetic chemist, thus inspiring a range of impressive and creative thought with regard to synthetic solutions," Wood says. "It is rising to meet these challenges that often leads chemists to the discovery of new methods and strategies, thus advancing the science of synthesis. Additionally, these efforts invariably result in an indomitable training for students."

Wood has earned a number of prestigious awards, including an Alfred P. Sloan Foundation Fellowship (1997), Novartis Chemistry Lectureship (1997­98), Parke-Davis Distinguished Michigan Lectureship (1997), Dreyfus Teacher-Scholar Award (1998), and Bristol-Myers Squibb Foundation Research Award (1998). Wood has received the prestigious Yamanouchi USA Faculty Award for five consecutive years (1998­2002).

Wood was chosen as the guest editor of the journal Tetrahedron for its "Symposia-in-Print" on new synthetic methods in December 1997. In late 2002, he joined the editorial board of Tetrahedron Letters.

When asked about how his academic career has developed and grown, Wood says: "It's been more about the successes of my students and working year after year with good, talented people. The Cope Scholar Award will hang on my office wall, and my photo will be in the article, but the credit really belongs to the students with whom I have worked."--NICK WAFLE

Arthur. C. Cope Senior Scholar Award


Hegedus
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Hegedus

Louis S. Hegedus's research centers on the development of organo-transition-metal compounds as reagents for organic synthesis, and he has been very successful at it. "Hegedus is one of a very small and elite group of senior scientists who played a critical role in introducing organometallic chemistry in stereoselective organic synthesis," according to a colleague.

Chemistry has always been what Hegedus wanted to do. "When I was young, I had a job at a YMCA camp, and something went nuts with the chemistry in the swimming pool. It had a black precipitate. I was fascinated," he recalls.

Hegedus received a B.S. in chemistry from Pennsylvania State University, State College, where he did undergraduate research with Albert Haim on coordination chemistry. He earned his Ph.D. from Harvard under E. J. Corey, where his interest in transition-metal organic chemistry got started. After postdoctoral work at Stanford with James P. Collman and a stint as a visiting scholar at the Royal Institute of Technology, Stockholm, Hegedus has worked in Colorado State University's department of chemistry, where he was named professor in 1980.

His early work made important contributions to the field of nickel- and palladium-catalyzed carbon-carbon bond-forming reactions. This work is said to have inspired other researchers to study organonickel chemistry and made popular the use of palladium in organic synthesis. One major area pursued by Hegedus was using Pd(II)-assisted nucleophilic additions to olefins, a method that proved useful for the synthesis of indoles and other nitrogen heterocycles. A key acheivement cited by Hegedus' colleagues was the synthesis of calvicipitic acid, one of the first syntheses to draw heavily on metal-catalyzed reactions in several steps.

Over the past two decades, however, Hegedus has focused on the photochemical reactions of chromium carbene complexes. As one colleague notes, the unprecedented observation that visible light photolysis of these complexes provides ketene-like activity sparked the discovery of many useful reactions, including the generation of b-lactams, dipeptides, nucleosides, a-amino acids, cyclobutanones, and dioxocyclams.

His current research involves the synthesis of antiviral nucleoside analogs using chromium carbene-derived optically active cyclobutanones, and also cyclams via chromium-carbene-derived azapenams. He says new methodologies with this technique are always evolving, and he tries to apply them to the synthesis of new biologically active compounds.

But Hegedus has had influence beyond this significant research. "Rarely has a scientist been as dedicated in educating others in his field," notes a colleague. "Hegedus has been a steadfast mentor and champion of younger generations of organometallic and synthetic chemists." He has done this by publication of texts that are seminal to the field and by continuing to teach classes, including sophomore organic chemistry. He is considered a star teacher within Colorado State University at both the undergraduate and graduate levels.

His scholarship continues in his long list of publications and service. Hegedus is currently an associate editor of the Journal of the American Chemical Society, and has served or is serving on the editorial board of many other research journals, including the Journal of Organic Chemistry, Organic Synthesis, and Organic Reactions. For 25 years (1973­ 98), he wrote the annual survey in the Journal of Organometallic Chemistry titled "Transition Metals in Organic Synthesis," a major effort.--DAVID HANSON

Larock
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Larock

Considered a pioneer in the use of palladium in organic synthesis, Richard C. Larock, 59, has contributed extensively to the development of important and useful synthetic methods that have rapidly been adopted by others. While organopalladium catalysis has been his main hallmark, he has contributed to other areas as diverse as developing new polymers from soybean oil.

Larock, university professor of chemistry at Iowa State University, has discovered a remarkable variety of new methodologies involving aryl, allylic, and vinylic palladium intermediates that have been widely employed by others to synthesize a tremendous range of organic compounds.

In doing so, he has notched up several "firsts." For example, he was the first to employ vinylic palladium intermediates in organic synthesis, an area in which he has been the most active researcher for nearly 30 years. He reported the first generation of vinylic palladium compounds, and subsequently published syntheses of 1,3- and 1,4-dienes; a, b-unsaturated acids and esters; butenolides; and enol esters from vinylpalladium species.

He also was the first to reveal the unique ability of palladium to migrate considerable distances along carbon chains to produce useful organic products. That behavior provides a novel approach to p-allyl- palladium compounds and a valuable way to couple aryl halides, nonconjugated dienes, and amines or carbon nucleophiles in a single synthetic process.

He has developed some useful palladium(II)-catalyzed cyclizations to form unsaturated lactones, isocoumarins, cyclic sulfonamides, 1,2-dihydroquinolines, 1,2-dihydroindoles, and benzopyrans. Moreover, he found that palladium(0) can be readily reoxidized by air or oxygen alone in the presence of dimethyl sulfoxide. That discovery, according to one colleague, has opened up some very exciting new chemistry, such as the catalytic conversion of enol silyl ethers to enones or enals.

A number of versatile annulation processes employing functionalized aromatic or vinylic halides or triflates plus dienes, unsaturated cyclopropanes, and alkynes to produce a multitude of useful heterocyclics have also emerged from his lab.

This annulation chemistry accommodates a wide range of functional groups, uses readily available unsaturated substrates, and proceeds under mild conditions in high yields to produce an extraordinary variety of products. Merck and Bristol-Myers Squibb have used Larock chemistry to prepare indole-based migraine headache drugs on a large scale, for example.

In fact, says one colleague, development of a suite of palladium-catalyzed heteroannulation reactions ranks among the most important contributions to ring construction during the past decade.

Larock graduated with a B.S. from the University of California, Davis, then earned his Ph.D. at Purdue University. His dissertation featured the mercuration of organoboranes. He was a postdoc at Harvard University under E. J. Corey.

In 1972, he joined the faculty at Iowa State University as an instructor of chemistry. He progressed up the ladder there to assistant professor and then associate professor of chemistry. He had a year's stint in 1985 as a visiting associate professor at the University of Hawaii, then returned to Ames as a full professor of chemistry and became university professor of chemistry in 1999.

Larock has authored four books on organic chemistry: two on organomercury chemistry and two editions of "Comprehensive Organic Transformations."--PATRICIA SHORT

Posner
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Posner

Anyone wanting to follow the progress of organic synthesis for the past four decades needs only to review Gary H. Posner's publications. Of course, that's no simple task as these include more than 250 papers, 22 patents, and a book.

While some make an academic career of superspecializing in one field, Posner takes pride in having made contributions in nearly every subspecialty of organic synthesis.

"Posner's career has been marked by an uncommon breadth that characterizes his amazing, encyclopedic knowledge of organic chemistry," says Thomas Lectka, a chemistry professor and colleague of Posner's at Johns Hopkins University. "His interests have spanned organocopper chemistry, total synthesis, heterogeneous reactions on zeolites, polycomponent condensation reactions, and steroid synthesis, and he has also made notable contributions to medicinal chemistry, including work on vitamin D-3 analogs and antimalarial compounds. Along the way, he has enriched the chemical literature with seminal contributions in all the aforementioned fields."

With his wide range of interests, it's not surprising that as an undergraduate, Posner considered careers in both biology and psychology. He was ultimately inspired to pursue chemistry by his organic chemistry professor, Robert Stevenson, at Brandeis University in Waltham, Mass. Posner says that it was organic chemistry's logic that appealed to him, adding, "The relevance of the subject to real-life issues was so persuasive and so powerful."

After graduating from Brandeis in 1964, Posner attended Harvard University. Under the direction of E. J. Corey, he earned his Ph.D. in 1968. He then spent a year as a research fellow with William G. Dauben at the University of California, Berkeley, before joining the faculty at Johns Hopkins University, where he is currently the Scowe Professor of Chemistry.

During the early years of his career, Posner garnered attention for his landmark contributions to organic synthesis using organocopper reagents. "Anyone doing this chemistry now owes a great debt to his trendsetting precedents from the 1970s and 1980s," Letcka says. Other notable synthetic methodologies soon followed, including the use of alumina as a reagent for catalyzing organic reactions and a four-component, one-pot synthesis of macrolides.

Even though he celebrated his 60th birthday in 2003, neither Posner's research nor his active lifestyle has flagged. "For the foreseeable future," he says, "I'm as excited about new discoveries and new science as I have been." He proudly reports that he plays racquetball with a partner 10 years his junior and currently runs a lab of more than a dozen students working on various synthesis projects and the medicinal chemistry of vitamin D-3 compounds and antimalarial drugs.

"Posner is clearly a leader in the field of synthetic chemistry of steroids and in particular the vitamin D molecules," remarks Hector F. DeLuca, a biochemistry professor at the University of Wisconsin, Madison. With regard to his antimalarial research, Lectka comments that Posner "has become committed in the most altruistic sense to the eradication of malaria worldwide."

Although he has been the recipient of numerous honors, including a Fulbright-Hays Senior Lecturer Award, 1987 Maryland Chemist of the Year Award from the ACS Maryland Local Section, and several student-nominated teaching awards, Posner says, "I think what I am most proud of is the array of graduate students and postdocs who have come through my lab over the years and allowed me to influence their lives a little bit."--BETHANY HALFORD

Suslick
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Suslick

Kenneth S. Suslick has made substantial contributions to the development of the supramolecular chemistry of porphyrins, their bioorganic and materials chemistry, their photochemistry and photophysics, their use as shape-selective oxidation catalysts, and their application as chemoresponsive sensors for artificial olfaction. In addition, he has pioneered the chemical applications of ultrasound. In both, he has demonstrated the high level of creativity and research leadership that is recognized by this award.

Suslick, 51, is William H. & Janet Lycan Professor of Chemistry and professor of materials science and engineering at the University of Illinois (UI), Urbana-Champaign, as well as founder and member of the board of directors of ChemSensing, Northbrook, Ill. Suslick started at UI as an assistant professor after earning a B.S. in chemistry with honors in 1974 from California Institute of Technology and a Ph.D. in chemistry in 1978 from Stanford University. He became an associate professor in 1984 and a full professor in 1988.

In the area of the supramolecular chemistry of porphyrins, "Suslick has repeatedly surprised the chemical community by identifying completely new applications with enormous practical potential," says Eric N. Jacobsen, chemistry professor at Harvard University. Suslick has discovered a new method of artificial olfaction, synthesized shape-selective oxidation catalysts with selectivities higher than cytochrome P450, developed the organic materials chemistry of porphyrins, used porphyrins for the first time as nonlinear optical materials, and modeled the photosynthetic reaction center using the photophysics of metalloporphyrin dimers. His recent invention of "smell-seeing," as reported in Nature, involves the use of metalloporphyrin microarrays as chemoresponsive sensors for vapor detection.

Suslick's research on the chemical effects of ultrasound "has fundamentally altered the way we think about the interactions of sound and matter," according to chemistry professor Steven C. Zimmerman at UI. When Suslick began his work in this area, "the field was relatively unknown to the chemical community," says John I. Brauman, chemistry professor at Stanford University. "Over the past decade," Brauman continues, "Suslick has created a new fundamental research area that has had a substantial impact on organic chemistry."

Suslick was the first to conduct experimental determinations of the conditions created during acoustic cavitation, mechanistic studies of the effects of ultrasound on heterogeneous reactions (for example, Grignards, lithiations, zinc and copper reactions), studies of sonochemistry and sonoluminescence of organometallic complexes, and sonochemical preparation of protein microspheres. His research led to the routine synthetic use of ultrasound for nearly all liquid-solid reactions, to a dozen U.S. patents, and to the formation of the start-up company VivoRx Pharmaceuticals (now American Pharmaceutical Partners).

Among Suslick's many awards are the American Chemical Society's 1994 Nobel Laureate Signature Award for Graduate Education, together with his student Mark Grinstaff; the Materials Research Society Medal; and a Special Creativity Award from the National Science Foundation. In addition, he was elected a fellow of the American Association for the Advancement of Science in 1993 and a fellow of the Acoustical Society of America in 1994. The editor or coeditor of four books and author or coauthor of more than 234 journal articles, Suslick has also reached a broader audience through publications such as Scientific American and New Scientist.

The award address will be presented before the Division of Organic Chemistry.--DEANNA MILLER

Arthur C. Cope Young Scholar Awards


Du Bois
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Du Bois

Before he settled on chemistry as a major, Justin Du Bois toyed with 10 other majors, from rhetoric to philosophy to physics. But happily, one of his teaching assistants at the University of California, Berkeley, helped Du Bois get a job in the lab of chemistry professor Kenneth N. Raymond. "I thought I was coming into the lab to do dishes," recalls Du Bois, who is now an assistant professor of chemistry at Stanford University. "But instead they had me running reactions. I got hooked."

After earning his B.S. in chemistry from Berkeley in 1991, Du Bois moved south to California Institute of Technology to attend graduate school. He signed on with a newly appointed assistant professor--Erick M. Carreira, now a professor of chemistry at the Swiss Federal Institute of Technology, Zurich--and proceeded to single-handedly complete the first synthesis of the cholesterol-reducing natural product zaragozic acid. He later developed a new class of manganese coordination complexes as reagents for the conversion of hydrocarbons to amines.

Du Bois earned his Ph.D. from Caltech in 1997, and he and Carreira were awarded the 1999 ACS Nobel Laureate Signature Award in Graduate Chemistry. He then went on to complete a two-year postdoc in the lab of Stephen J. Lippard at Massachusetts Institute of Technology before joining the Stanford faculty.

At Stanford, Du Bois has created a research program that combines fundamental methodological studies with cutting-edge natural product synthesis. Among his first accomplishments have been the development of novel methods for the selective oxidation of saturated C­H bonds. "These elegant and innovative processes enable facile assembly of 1,2- and 1,3-difunctionalized amine derivatives from simple alcohol starting materials," notes Du Bois's Stanford colleague Barry M. Trost. Du Bois's methodology should find widespread use, Trost contends, pointing out that his own synthesis of the sugar callipeltoside takes only six steps with the Du Bois reaction, compared to 14 steps without it. More recently, Du Bois has found a simple way to selectively aziridinate alkenes.

"These reactions have the potential to dramatically alter the strategy of organic synthesis," Carreira says. "Because of Du Bois's chemistry, an amine need not be prepared from an olefin, an imine, an alcohol, or a carbonyl anymore."

Du Bois himself hopes to use his metal-catalyzed C­H bond functionalization reactions to synthesize neuroactive natural products as well as therapeutically or biochemically useful derivatives. To that end, his group has reported syntheses of manzacidins A and C, members of a class of natural products that inhibit serotonin receptors. Du Bois's methods for C­H bond functionalization allowed his group to synthesize the substituted tetrahydropyrimidine core of the manzacidins, which are no longer available from indigenous sources.

Du Bois's more recent asymmetric synthesis of tetrodotoxin, the guanidinium poison found in the Japanese fugu, or blowfish, has provided another showcase for his methods. Tetrodotoxin has found widespread use as a probe to interrogate the structure and function of voltage-gated sodium ion channels. "Access to targets such as these will facilitate Du Bois's group's future efforts to prepare select analog compounds," Trost notes. "These studies will place his program in a truly unique position to interface complex chemical synthesis with research in the neurological sciences," he adds.

Already, Du Bois's independent accomplishments have earned him a Camille & Henry Dreyfus New Faculty Award as well as young investigator awards from the Beckman Foundation, Pfizer, Boehringer Ingelheim, Eli Lilly, GlaxoSmithKline, and Bristol-Myers Squibb.--AMANDA YARNELL

Liu
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Liu

"I've been interested in science since before I was old enough to define 'science,'" says David R. Liu, 30, associate professor of chemistry and chemical biology at Harvard University. "Some of my earliest childhood memories include mixing various household materials to observe simple but exciting reactions take place, watching insects communicate, and playing with mirrors."

An organic chemistry class in his freshman year at Harvard "inspired a deep desire to study the chemistry behind life," Liu says. "I was fortunate enough to engage in research in E. J. Corey's group for three years following this course; this undergraduate research experience and E. J.'s mentorship really crystallized my interests in organic chemistry."

Gregory L. Verdine, Liu's colleague at Harvard, has known Liu since his days as an undergraduate. "Even at that time, he stood out as an exceptionally intelligent and talented individual, outperforming our entire graduate class in advanced graduate-level courses during his sophomore year, and completing essentially a Ph.D.'s worth of work as a member of E. J. Corey's lab," Verdine says. Graduating summa cum laude, Liu was the valedictorian of the 1994 class at Harvard, an honor rarely achieved by science students.

While working on his Ph.D. in Peter Schultz's lab, Liu says he "came to appreciate powerful aspects of molecular biology, including the ability of proteins and nucleic acids to evolve in nature or in the laboratory toward desired properties." He received his Ph.D. from the University of California, Berkeley, in 1999.

Liu returned to Harvard in 1999 as an assistant professor. He was promoted to associate professor in 2003 and named the John L. Loeb Associate Professor of Natural Sciences.

In his research program at Harvard, he is using the evolutionary abilities of nucleic acids in a technique known as DNA-templated synthesis, in which short sequences of DNA are used to direct a series of reactions.

"I first became interested specifically in DNA-templated synthesis as a means of applying molecular evolution concepts to synthetic molecules when writing my preliminary examination proposal at the end of my first year of graduate school at Berkeley in 1995," Liu says. "In fact, our earliest work in the DNA-templated synthesis area simply implemented some of the experimental concepts described in that proposal."

"David's first few papers on this subject represent a manifesto for the founding of a new field," Verdine says. "To be fair, others had carried out DNA-templated reactions before, but those invariably entailed closure of the DNA backbone. David's system, by contrast, involves the transmission of the coding information in the DNA backbone into a series of programmed reaction steps. I find it simply stunning that he has been able to conduct multistep organic synthesis on a sub-nanomole scale, an unprecedented feat of synthetic prowess."

Matthew D. Shair, another Harvard colleague, is equally generous with his praise of Liu. "For years, chemists have dreamed of being able to apply the evolutionary principles used by nature to the discovery of small molecules with desired properties such as protein binders or catalysts. Liu is building a foundation, brick-by-brick, that may lead to this 'holy grail' of chemistry," he says. "Even without reaching his final goal, Liu has already made important contributions to organic chemistry. If he is successful in achieving evolution of small molecules, he will usher in a new era in chemistry."

"The field of organic chemistry/chemical biology has not been privileged to count as one of our own a person of David's talent in quite some time," Verdine says. "He is a scholar of the highest order, a deep and innovative thinker, and an inspiration to young people who might otherwise have been drawn to flashier fields than chemistry."--CELIA HENRY

WHO IS ARTHUR C. COPE?
Arthur C. Cope (1909­66) was a pioneering and indefatigable chemist whose research involved chemistry of medium-sized ring compounds, transannular reactions, rearrangement of allyl groups in three-carbon systems, and work in synthetic organic chemistry. He was a chairman of the chemistry department of Massachusetts Institute of Technology (1945­64). He was also a tireless contributor to ACS, serving as its president (1961) and chair of the board (1959, 1960, and from 1962 until his death). In 1972, the ACS Board of Directors accepted responsibility for administering awards created under the terms of Cope's will.

Frank H. Field & Joe L. Franklin Award for Outstanding Achievement in Mass Spectrometry


Sponsored by Bruker Daltonics

Kenneth G. Standing, 78, emeritus professor in the department of physics and astronomy at the University of Manitoba, in Canada, made the switch from nuclear physics to mass spectrometry in 1979.

"More than 20 years ago, Ken saw the light and converted from nuclear physics to mass spectrometry," says Marvin L. Vestal of Applied Biosystems, Framingham, Mass. "He brought with him a thorough knowledge of basic physics and electronics, gleaned from developing exotic instruments for studying high-energy atomic ions, and applied that knowledge and insight to developing revolutionary instrumentation and techniques for measurements on molecules."

"I changed to mass spectrometry," Standing says, "because I had developed an interest in biology, and mass spectrometry offered a chance to apply the expertise that I had developed in physics to that field. Nuclear physics had become a much more mature area by that time, and I found it less appealing."

His physics background was helpful in the switch to mass spectrometry. "Many of the methods now used in time-of-flight [TOF] mass spectrometry have been derived from earlier developments in nuclear physics, so my nuclear physics background was invaluable," Standing explains. "I had already been involved in experiments measuring neutron time of flight."

In the mass spectrometry community, Standing is best known for his work in developing instrumentation for time-of-flight mass analysis. Vestal says Standing "has been a major force in establishing the TOF mass spectrometer as the preferred technique for many applications to large nonvolatile molecules of biological importance."

Standing created the collisional-damping interface for orthogonal injection TOF mass spectrometry that made it practical to build hybrid mass spectrometers combining quadrupoles with high-performance TOF analyzers. "For the first time, both [electrospray] and MALDI were available on a single high-performance instrument," Vestal says. "Since John Fenn and Koichi Tanaka recently shared the Nobel Prize in Chemistry in 2002 for these important achievements, it seems appropriate that Ken Standing should be recognized for developing the most important instrument that makes these ionization techniques available for routine applications."

Peter Roepstorff, a professor in the department of biochemistry and molecular biology at the University of Southern Denmark, Odense, calls Standing a pioneer in mass spectrometry of biological macromolecules. "He used his background in nuclear physics and skills in instrument design and building to demonstrate the possibilities for analysis of such molecules long before commercial instruments became available. His home-built instruments have served as models for many of the later commercially available instruments."

Richard M. Caprioli, director of the mass spectrometry research center at Vanderbilt University Medical Center, agrees. "Instruments derived from his work have made a major contribution to the acceptance of mass spectrometry by the biological community as an essential research tool," he says.

Standing received his bachelor's degree in physics from the University of Manitoba in 1948. He received his master's and doctoral degrees in physics from Princeton University, where he worked with Rubby Sherr, in 1950 and 1955, respectively.

He has been a professor at the University of Manitoba since 1953, when he joined the faculty as an assistant professor. He was promoted to associate and full professor in 1959 and 1964, respectively. In 1995, he became professor emeritus. In 1998, Standing received the Award for Distinguished Contributions to Mass Spectrometry from the Canadian Society for Mass Spectrometry. Although he retired in 1993, he intends to continue doing research as long as he is able.

The award address will be presented before the Division of Analytical Chemistry.--CELIA HENRY

 
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