Studies on Iejimalide B: Preparation of the Seco Acid and Identification of the Molecule's “Achilles Heel”

Authors


  • Generous financial support from the MPG, the Fonds der Chemischen Industrie, the Alexander-von-Humboldt Foundation (fellowship to C.N.), and the NSERC, Canada (fellowship to M.T.) is gratefully acknowledged. We thank Dr. R. Riveiros for assistance in the initial phase of this project, and Dr. R. Mynott, B. Gabor, and C. Wirtz for their invaluable help with the structure assignment of several key compounds.

Abstract

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Limitations of models in total synthesis are illustrated by a study towards the potent cytotoxic macrolide iejimalide B. Although the Yamaguchi protocol allowed for the esterification of elaborate segments, attempted macrolactonization of the seco acid met with failure (see scheme, Boc= tert-butyloxycarbonyl). The assembly of the seco acid involves some of the most advanced applications of the Julia olefination known to date.

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