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Synthesis of (-)-5-epi-Vibsanin E
B. D. Schwartz, J. R. Denton, Y. Lian, H. M. L. Davies*, C. M. Williams*
University of Queensland, Brisbane, Australia; University at Buffalo, State University of New York and Emory University, Atlanta, USA
20 November 2009 (online)
The key feature of this synthesis is the construction of the seven-membered ring by a formal [4+3] cycloaddition. The reaction proceeds via an asymmetric cyclopropanation of diene A with a vinylcarbenoid derived from B to form a divinylcyclopropane C which then undergoes a Cope rearrangement to form the cycloheptatriene D.