Stereochemical revision of communiols D and H through synthesis

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    11 Citations (Scopus)

    Abstract

    Based on the previously revised stereochemistries for communiols A-C, the ent-8-epi- and ent-6-epi-stereoisomers of the original structures proposed for communiols D and H, respectively, were synthesized as highly probable candidates for their genuine structures by using the Sharpless asymmetric dihydroxylation as the source of chirality. Complete accord in spectral properties between each synthetic candidate and the corresponding natural material as well as the fact that communiols A-D and H were all isolated from the same fungal source, led us to the conclusion that the stereochemistries of communiols D and H should also be revised to their (3S,5S,7R,8S,11R)- and (5S,7R,8S)-forms, respectively.

    Original languageEnglish
    Pages (from-to)1102-1109
    Number of pages8
    JournalTetrahedron
    Volume62
    Issue number6
    DOIs
    Publication statusPublished - 2006 Feb 6

    Keywords

    • Asymmetric dihydroxylation
    • Communiol
    • Dioxabicyclo[3.3.0]octane
    • Enantioselective synthesis
    • Podospora communis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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