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Paper | Special issue | Vol 82, No. 2, 2011, pp.1379-1409
Published online: 13th August, 2010
DOI: 10.3987/COM-10-S(E)93
■ A Cyclic Acetal Tethered Intramolecular Diels-Alder Cycloaddition. Studies Directed toward a Total Synthesis of (±)-Fusidilactone C

Sunil K. Ghosh, Yonggang Wei, Aleksey I. Gerasyuto, John B. Feltenberger, Jiashi Wang,* and Richard P. Hsung*

*Department of Chemistry, Division of Pharmaceutical Sciences, University of Wisconsin, 777 Highland Aenue, Madison, WI 53705-2222, U.S.A.

Abstract

Efforts toward a synthesis of (±)-fusidilactone C is described here featuring a novel cyclic acetal tethered intramolecular Diels-Alder strategy. This unique and facile IMDA turned out to be highly endo-selective [endo-I and endo-II], as assessed from our mechanistic analyses. When using protic solvents or Lewis acids, the endo-I selectivity was greatly enhanced. Thus, it proved to be a real challenge to circumvent this excellent stereochemical outcome, which is undesired for the total synthesis, as an exo-II selectivity is desired. Progress was made to use the endo-II cycloadduct and to access the desired trans-2-oxadecalin motif in (±)-fusidilactone C.

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