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Roger Adams Award In Organic Chemistry

by Stu Borman
February 25, 2013 | A version of this story appeared in Volume 91, Issue 8

Credit: Courtesy of David Evans
This is a mug of Harvard University Chemistry Professor David A. Evans.
Credit: Courtesy of David Evans

Sponsored by Organic Reactions Inc. and Organic Syntheses Inc.

Organic synthetic research by Harvard University chemistry professor David A. Evans “has been critical to the dramatic developments in the field of asymmetric synthesis over the last 30 years,” says Erick M. Carreira of the Swiss Federal Institute of Technology, Zurich. “Evans’ work is distinguished in its fundamental contributions to science as well as its versatility and practicality.”

Asymmetric synthesis is the chirally selective form of organic synthesis. Evans wins this year’s Roger Adams Award for having developed asymmetric synthesis auxiliaries (chirality-directing agents) and catalysts that are “indispensable in academic and industrial laboratories,” according to his award citation.

Over the past 45 years, the central theme of Evans’ research has been the development of reaction methodology to achieve absolute stereocontrol in carbon-carbon bond-forming reactions. His group was first to achieve the de novo synthesis of complex natural products via the exclusive use of chiral auxiliaries to control stereochemistry. This was a significant departure from the traditional practice of relying predominantly on the “chiral pool” of existing compounds as a source of stereochemical elements of target structures.

“Evans’ auxiliaries and catalysts for asymmetric bond construction have become some of the most reliable and efficient systems for asymmetric synthesis in academic and industrial laboratories,” Carreira says.

Evans has devised more than 50 highly efficient and innovative syntheses of complex natural products. These compounds include the polyketides macbecin, tylonolide, bafilomycin, oleandolide, 6-deoxyerythronolide B, calcimycin, X-206, ionomycin, cytovaricin, and ferensimycin; the β-lactam antibiotic thienamycin; the peptide antibiotic vancomycin; the phenolics tetrahydrocannabinol and colchicine; and the alkaloids cyanocycline and histrionicotoxin.

Evans, 71, was born in Washington, D.C. He earned a bachelor’s degree from Oberlin College in 1963 and a Ph.D. in chemistry in 1967 from California Institute of Technology, where he worked in the research group of the late Robert E. Ireland. Evans then joined the faculty at the University of California, Los Angeles. In 1974, he returned to Caltech, and in 1983 he moved to Harvard, where he served three years as chair of the department of chemistry and chemical biology. Evans is currently the Abbott & James Lawrence Research Professor of Chemistry at Harvard.

“I am sure that 50 years henceforth students will know and use Evans’ chemistry,” Carreira says. “Future investigators will rely on the fundamental principles and insights delineated by Evans as the basis for the next generation of new reactions.”

Evans will present the award address at the National Organic Chemistry Symposium in Seattle in June.



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