Chemistry Seminar Series

Wed, 28 Nov 2018
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Dr. P. Andrew Evans

Queen's University

New Vistas in the Asymmetric Construction of C-C Bonds: Total Synthesis of Complex Bioactive Agents

Wednesday, November 28, 2018
B9201 @ 3:30 p.m.

Host: Dr. Robert Britton

Abstract

The seminar will describe the development and application of stereoselective transition metal-catalyzed cross-coupling and cycloaddition reactions for the total synthesis of bioactive agents. [1,2] Specifically, it will outline our approach to the construction of acyclic quaternary carbon stereogenic centers and to the development of a concise, efficient and scalable total synthesis of the complex bioactive sesquiterpene natural product, thapsigargin. [3] Hence, the first part will focus on a series of new metal-catalyzed allylic cross-coupling reactions with novel pronucleophiles [4,5] and the second part will outline the development of higher-order carbocyclization reactions that emulate terpene biosynthesis. [6]

References

1. Oliver, S.; Evans, P. A. Synthesis 2013, 45, 3179.

2. Inglesby, P. A.; Evans, P. A. Chem. Soc. Rev. 2010, 39, 2791.

3. (a) Chen, D.; Evans, P. A. J. Am. Chem. Soc. 2017, 139, 6046.

4. (a) Evans, P. A.; Oliver, S.; Chae, J. J. Am. Chem. Soc. 2012, 134, 19314. (b) Turnbull, B. W. H.; Oliver, S.; Evans, P. A. J. Am. Chem. Soc. 2015, 137, 15347. (c) Turnbull, B. W. H.; Chae, J.; Oliver, S.; Evans, P. A. Chem. Sci. 2017, 8, 4001.

5. (a) Evans, P. A.; Clizbe, E. A.; Lawler, M. J.; Oliver, S. Chem. Sci. 2012, 3, 1835. (b) Turnbull, B. W. H.; Evans, P. A. J. Am. Chem. Soc. 2015, 137, 6156. (c) Wright, T. B.; Evans, P. A. J. Am. Chem. Soc. 2016, 138, 15303.

6. (a) Evans, P. A.; Inglesby, P. A. J. Am. Chem. Soc. 2008, 130, 12838. (b) Evans, P. A.; Inglesby, P.  A.  J. Am. Chem. Soc. 2012, 134, 3635. (c) Mazumder, S.; Shang, D.; Negru, D. E.; Baik, M.-H.; Evans, P. A. J. Am. Chem. Soc. 2012, 134, 20569. (d) Inglesby, P.A.; Bacsa, J.; Negru, D. E.; Evans, P. A. Angew. Chem. Int. Ed. 2014, 53, 3952. (e) Evans, P. A.; Negru, D. E.; Shang, D. Angew. Chem. Int. Ed. 2015, 54, 4768.

Biography

P. Andrew Evans is the Alfred R. Bader Chair of Organic Chemistry and a Tier 1 Canada Research Chair in Organic and Organometallic Chemistry in the Department of Chemistry at Queen’s University. He received a B.Sc. with honors in Applied Chemistry at Newcastle Polytechnic in 1987 and a Ph.D. at the University of Cambridge in 1990 under the supervision of Andrew B. Holmes, FRS. He then completed postdoctoral studies with Philip D. Magnus, FRS, at the University of Texas at Austin as a NATO Postdoctoral Fellow. In 1993 he initiated his independent career at the University of Delaware, where he rose through the ranks to Professor before moving to Indiana University in 2001. In 2006, he moved to the University of Liverpool where he was the Heath Harrison Chair of Organic Chemistry before moving to his current position in July 2012. Recent awards include the ACS Cope Scholar Award, RSC Pedler Award, Royal Society Wolfson Research Merit Award, Pfizer Award for Creativity in Organic Chemistry, Johnson and Johnson Focused Giving Award, GlaxoWellcome Chemistry Scholar Award, Camille Dreyfus Teacher-Scholar Award, Eli Lilly Grantee Award and Zeneca Excellence in Chemistry Award. He has also served on ACS Division of Organic Chemistry as a Member-at-Large; Councilor, National Organic Symposium Executive Officer and Chair. Additionally, he has also served on the Chem. Comm. Editorial Board, an Associate Editor for Synthesis and as a Responsible Editor for Organic Reactions, where he recently assumed the role as Editor-in-Chief. He has published more than 125 papers, articles, reviews, book chapters and monographs, in addition to delivering over 500 plenary and invited lectures.

Professor P. Andrew Evans
Department of Chemistry
Queen's University
Email: andrew.evans@chem.queensu.ca
Web: http://faculty.chem.queensu.ca/people/faculty/evans/index.htm