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Ernest Guenther Award In The Chemistry Of Natural Products

Recipients are honored for contributions of major significance to chemistry

by Patricia L. Short
January 26, 2009 | A version of this story appeared in Volume 87, Issue 4

Credit: Courtesy of Peter Wipf
Credit: Courtesy of Peter Wipf

Sponsored by Givaudan

Peter Wipf, a 49-year-old University Professor of Chemistry at the University of Pittsburgh, is this year's recipient, in recognition of "his outstanding work in natural product synthesis and structure determination," according to his nominators.

Wipf's contributions focus heavily on the total synthesis of natural products. His work is described in more than 310 publications and patents that range from classical total synthesis to ab initio computations.

He has completed about 30 total syntheses of complex natural products, including, most recently, bistramide, leucascandrolide, and tuberostemonine.

His total syntheses also served as a launching pad for the design of new methods in azole chemistry. That work, in turn, was further refined in total syntheses of thiangazole and muscoride A, according to colleague Larry Overman, Distinguished Professor of Chemistry at the University of California, Irvine.

Wipf accomplished the first total synthesis of the pentacyclic alkaloid tuberostemonine from a hydroindole intermediate that is readily obtained by oxidative cyclization of carbobenzoxy-protected L-tyrosine. The single stereocenter of the amino acid precursor was relayed into nine of the 10 stereogenic carbons of the target molecule. The tuberostemonine synthesis also highlighted a threefold use of ruthenium catalysts: in azepine ring-closing metathesis, in alkene isomerization, and in cross-metathesis propenyl-vinyl exchange.

Among his recent projects has been to use natural products as the basis for rational structure-function correlations showing the chemical change of antibiotic properties of gramicidin S into reactive oxygen-scavenging activity. The resulting de novo-designed agent showed in vivo efficacy against hemorrhagic shock and neurodegenerative diseases.

His discovery of a silver cluster complex of westiellamide was the first concrete report on the fascinating bioinorganic chemistry of these marine natural products, according to Overman.

Wipf studied chemistry at the University of Zurich, earning his Dipl. Chem. and Ph.D. in 1984 and 1987, respectively. He was a Swiss National Science Foundation Postdoctoral Fellow in the University of Virginia's department of chemistry from 1988 to 1990.

His first professional post was an assistant professorship at the University of Pittsburgh, from 1990 to 1995. Since then, he has continued to progress at Pittsburgh, becoming University Professor of Chemistry in 2004. Since 1997, he has been director of the Combinatorial Chemistry Center, and since 2002, he has been director of the university's Center for Chemical Methodologies & Library Development. And since 2001, he has been a professor of pharmaceutical sciences at the university's School of Pharmacy.

Along the way, Wipf has been made a fellow of a variety of societies, including the American Association for the Advancement of Science and the U.K.'s Royal Society of Chemistry. In addition, he has collected a number of awards and visiting professorships.

Another colleague, Thomas R. Hoye, a professor of chemistry at the University of Minnesota, says Wipf's rise to prominence in the field of natural product chemistry "has been nothing short of spectacular."

The most distinctive and pioneering of all of Wipf's natural product research, Hoye says, puts to work his intuition in demonstrating that computational methods are sufficiently reliable to be used to assist in complex structure assignments. As Wipf now has begun to show, further computation of various NMR properties is potentially even more powerful, Hoye adds.

Wipf will present the award address before the Division of Organic Chemistry.


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