Phi Lambda Upsilon Xi Chapter - University of Pittsburgh Francis Clifford Phillips Lecture Series 1985 Phillips Lecturer Brief Biography of David Evans David Albert Evans was born in Washington D.C. in 1941. He received his A.B. degree from Oberlin College in 1963. He obtained his Ph.D. at the California Institute of Technology in 1967, where he worked under the direction of Professor Robert E. Ireland. In that year he joined the faculty at the University of California, Los Angeles. In 1973 he was promoted to the rank of Full Professor and shortly thereafter returned to Caltech where he remained until 1983. In 1983 he joined the Faculty at Harvard University and in 1990 he was appointed as the Abbott and James Lawrence Professor of Chemistry. In July of 1998 he completed his three-year term as chair of the Harvard Department of Chemistry and Chemical Biology. Professor Evans is a recipient of numerous honors such as the ACS Award for Creative Work in Synthetic Organic Chemistry (1982), and the Arthur C. Cope Scholar Award (1988), the Yamada Prize (1997), the Tetrahedron Prize (1998), the Robert Robinson Award (1998), the Prelog Medal (1999), and the Arthur C. Cope Award (2000). He was elected into the National Academy of Sciences in 1984, the American Academy of Arts and Sciences in 1988 and the Royal Society of Chemistry in 2001. He is currently a consultant with Merck Research Laboratories and with Oxford Asymmetry. He has been on the Advisory Boards of The Journal of the American Chemical Society, Tetrahedron, Tetrahedron Letters, and Topics in Stereochemistry. Currently, he is on the Advisory Boards of Organic Letters and Current Opinion in Bio-organic Chemistry, London, UK Evans has made fundamental advances in the design of stereoselective reactions and the applications of these reactions to natural products synthesis. Over the last two decades, reaction methodology directed toward achieving absolute stereocontrol in carbon-carbon bond forming reactions has been one of the central themes that has been developed in his laboratory. Enantioselective Diels-Alder, Michael, and aldol reactions are but three of the important families of processes developed in his group. In the area of synthesis design, Evans was the first to achieve the de novo synthesis of complex natural products through the exclusive use of chiral auxiliaries to control stereochemical relationships. This represented a dramatic departure from the more prevalent reliance on the "chiral pool" for the origins of absolute stereocontrol within the target structure. Evans' chiral auxiliaries and chiral catalysts for enantioselective bond constructions are widely used in both industrial and academic laboratories throughout the world. Over the last three decades, the Evans group has synthesized more than forty complex natural products. Recent ground-breaking synthesis from the Evans Laboratory include the synthesis of vancomycin, bryostatin, and altohyrtin C. Some of the significant advances in reaction methodology coming from the Evans labotratory are summarized below: 1971 Introduced the allylic transposition of sulfoxides and alcohols (Mislow-Evans Rearr). 1973 Discovered the catalyzed addition of cyanosilanes to ketones, quinones and aldehydes. 1974 Discovered the utility of metallated allylic ethers as homoenolate equivalents. 1975 Discovered the oxy-anionic substituent effect in the oxy-Cope rearrangement. 1979 Discovered the utility of boron enolates in stereoselective aldol reactions. 1980 Revealed the utility of the Tebbe Reagent for ester methylenation (with R. Grubbs). 1980 Introduced zirconium enolates in stereoselective aldol reactions. 1980 Introduced chiral oxazolidinones as carboxylic acid-derived auxiliaries for enantioselective alkylation, aldol, and acylation reactions. 1985 Introduced chiral oxazolidinones as auxiliaries for Diels-Alder reactions. 1985 Introduced chiral oxazolidinones as auxiliaries for the enantioselective Staudinger synthesis of b-lactams. 1986 Introduced enolate electrophilic amination concept for the enantioselective synthesis of a-amino acids. 1986 Applied chiral oxazolidinones to the enantioselective synthesis of b-hydroxy-a-amino acids. 1990 Introduced the samarium-promoted intramolecular Tishchenko reduction. 1991 Introduced chiral bis(oxazoline) ligands for enantioselective olefin cyclopropanation. 1991 Introduced soluble copper complexes as effective catalysts for olefin aziridination. 1993 Introduced chiral bis(oxazoline)-Cu(II) complexes as catalysts for enantioselective olefin aziridination. 1993 Introduced chiral bis(oxazoline)-Cu(II) Complexes as chiral catalysts for the enantioselective Diels-Alder Reaction. 1993 Introduced a chiral samarium-based catalyst for the asymmetric Meerwein-Ponndorf-Verley reduction. 1996 Introduced C2-symmetric Cu(II) complexes as chiral Lewis acids for enantioselective aldol additions of silylketene acetals to benzyloxyacetaldehyde. Natural products Syntheses completed by the Evans Group. Alkaloids. Luciduline, Cherylline, Dihydrocannivonine, Perhydrohistrionicotoxin, Colchicine, Cyanocycline Terpenes. Bakkenolide-A, b-Dolabrin, Juvabione, Tetrahydrocannabinol, a-Himachelene Macolide Antibiotics. Macbecin I, A83543A (Lepicidin), Tylonolide, Rutamycin B, Bafilomycin A1, Oleandolide, 6-Deoxyerythronolide B, elaiophylin aglycon Ionophore Antibiotics. A-23187 (Calcimycin), Antibiotic X-206, Premonensin, Ionomycin, Cytovaricin, Lonomycin A (Emericid), Ferensimycin B Amino Acid-Derived Natural Products. Carbacephalosoporin, PS-5, Thienamycin, Echinocandin D, OF4949-III, K-13, Diphthamide, Orienticin C (Bis-dechlorovancomycin) aglycon Marine Natural Products. Calyculin A, Isopulo'upone, Miyakolide Miscellaneous Structures. Zaragozic Acid C, ent-Shikimic acid, Cinatrin C1 and C3 Internet: http://www.chem.harvard.edu/ [About PLU] [History] [Purpose] [Members] [Minutes] [Phillips Lecture] [Upcoming Events] [To Contact Us] [Home] This page was last revised on September 16, 2002.