The 25th ISHC Congress–Santa Barbara CA Aug 23-28, 2015
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Title:
Development of New Higher-Order Carbocyclization Reactions: Emulating Terpene
Biosynthesis
Abstract: (Your abstract must use Normal style and must fit into the box. Do not enter author details)
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 -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.