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Biomimetic Syntheses from Squalene-Like Precursors: Synthesis of ent-Abudinol B and Reassessment of the Structure of Muzitone

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posted on 2010-04-14, 00:00 authored by Matthew A. Boone, Rongbiao Tong, Frank E. McDonald, Sheri Lense, Rui Cao, Kenneth I. Hardcastle
We achieved the stereoselective syntheses of two different structural patterns corresponding to the enantiomers of the marine natural products abudinol B and muzitone, by developing two-directional tandem biomimetic cyclizations of polyepoxides of squalene analogues in which one alkene was functionalized as an enolsilane. In the course of this work, we demonstrated that the structure of muzitone was misassigned.