Synfacts 2009(12): 1312-1312  
DOI: 10.1055/s-0029-1218334
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-5-epi-Vibsanin E

Contributor(s): Philip Kocienski
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
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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.