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Monday, August 24 • 2:00pm - 2:40pm
[0202] Development of New Higher-Order Carbocyclization Reactions: Emulating Terpene Biosynthesis

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Limited Capacity seats available

Transition metal-catalyzed higher-order carbocyclization reactions provide powerful methods for the stereoselective construction of complex polycyclic systems that are generally not accessible via classical pericyclic reactions.[1]  We have demonstrated the merit of the rhodium-catalyzed [m+n+n] carbocyclization reactions of carbon and heteroatom tethered 1,6-enynes with carbon monoxide, alkynes and dienes.  More recently we have explored the development of a stereoselective rhodium-catalyzed [3+2+2] carbocyclization of 1,6-alkenylidenecyclopropanes with activated alkynes for the construction of cis-fused bicycloheptadienes,[2] which prompted the isolation of the key metallacycle intermediate[3] and the expansion of the scope of p-fragments to carbon monoxide and allenes.[4,5]  The seminar will outline some of these developments and their application to challenging bioactive natural products.

References

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

2.  (a) Evans, P. A.; Inglesby, P. A. J. Am. Chem. Soc. 2008, 130, 12838.  (b) Evans, P. A.; Inglesby, P. A.; Kilbride, K. Org. Lett. 2013, 15, 1798.  (c) Evans, P. A.; Negru, D. E.; Shang, D. Angew. Chem. Int. Ed. 2015, 54, 4768.

3.  Inglesby, P. A.; Bacsa, J.; Negru, D. E.; Evans, P. A. Angew. Chem. Int. Ed. 2014, 53, 3952.

4.  Mazumder, S.; Shang, D.; Negru, D. E.; Baik, M.-H.; Evans, P. A. J. Am. Chem. Soc. 2012, 134, 20569.

Invited Lecturers
avatar for P. Andrew Evans

P. Andrew Evans

Professor and Alfred R. Bader Chair of Organic Chemistry, Queen's University


Monday August 24, 2015 2:00pm - 2:40pm
Corwin West