Enantioselective total synthesis and stereochemical revision of communiols E and F

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Abstract

The enantioselective total synthesis of candidate structures for communiols E and F, novel bicyclic polyketides of fungal origin, was accomplished using a Lewis acid-mediated ring closure reaction of an allylsilane intermediate as the key step. Comparison of the spectral data of the synthetic materials with those of natural communiols E and F, coupled with biosynthetic considerations, led to the conclusion that the stereochemistry of communiols E and F should be (2S,5S,TR, 8S,11R)- and (5S,7R,8S,11R)-forms, respectively.

Original languageEnglish
Pages (from-to)6287-6290
Number of pages4
JournalJournal of Organic Chemistry
Volume71
Issue number16
DOIs
Publication statusPublished - 2006 Aug 1

ASJC Scopus subject areas

  • Organic Chemistry

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