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A Formal Synthesis of Vinigrol

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  • We thank the NSERC, Merck Frosst Canada, and the University of Ottawa for generous funding. C.M.G.-B. thanks NSERC and the Government of Ontario for postgraduate scholarships (CGS-D and OGSST). J.P. thanks the Gouvernement du Québec for a postgraduate scholarship (FQRNT). We thank Dr. I. Korobkov for X-ray analysis. We are grateful to Prof. M. Sherburn (Australian National University) and Prof. P. Baran (Scripps) for helpful discussions.

Abstract

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Two key reactions in a rapid assembly of the tricyclic core of vinigrol are a stereoselective Claisen rearrangement and an intramolecular Diels–Alder reaction. The method paves the way for a total synthesis of this synthetically challenging and biologically interesting natural product.

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