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

Date: 
Tuesday, November 27, 2018 - 12:45 to 14:00
Speaker: 
Dr. P. Andrew Evans
Affiliation: 
Department of Chemistry, Queen’s University
Event Category: 
LMC - Lectures in Modern Chemistry
Location: 
Chemistry B250

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.