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Studies towards Simalikalactone D and Quassimarin: Construction of an Advanced Pentacyclic Intermediate

✍ Scribed by Tony K. M. Shing; Xue Y. Zhu; Yeung Y. Yeung

Publisher: John Wiley and Sons
Year: 2003
Tongue: English
Weight: 341 KB
Volume: 9
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200305158

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✦ Synopsis

Abstract

An advanced pentacyclic intermediate, amenable to further elaboration into the target molecules simalikalactone D and quassimarin, has been synthesized from (S)‐(+)‐carvone in 21 steps and with an overall yield of 12 %. The synthesis is efficient, stereocontrolled, enantiospecific, and chirality productive, creating eight new chiral centres in pentacycle, and should provide opportunities for rapid access to simalikalactone D analogues and other bioactive quassinoids. The reaction sequence involves a regioselective bishydroxylmethylation, a stereocontrolled epoxidation, an epoxymethano‐bridge formation, a 1,3‐sigmatropic rearrangement and an intramolecular Diels–Alder reaction as the key steps.

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