Synthesis and stereochemistry of glaucoposterol A and strophasterol D

Shuntaro Sato, Yuka Taguchi, Shigefumi Kuwahara

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    1 Citation (Scopus)

    Abstract

    The proposed structure of glaucoposterol A, a strophastane-type steroid of mushroom origin, has been synthesized from an aldol obtained in our previous synthesis of strophasterol F, a diastereomer of the proposed structure of glaucoposterol A. Based on the fact that the NMR data of natural glaucoposterol A are distinctly different from those of the synthetic material, but matches those of strophasterol F, we put forward a proposal that glaucoposterol A and strophasterol F are actually the same compound. In addition, the hitherto unknown stereochemistry of strophasterol D has been elucidated through synthesis of its two diastereomeric structures.

    Original languageEnglish
    Article number131129
    JournalTetrahedron
    Volume76
    Issue number17
    DOIs
    Publication statusPublished - 2020 Apr 24

    Keywords

    • Cycloaddition
    • Stereochemical determination
    • Steroid
    • Strophasterol
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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