Enantioselective total synthesis of (+)-bucidarasins A and C

Kenji Usui, Masahisa Nakada

    Research output: Contribution to journalArticle

    3 Citations (Scopus)

    Abstract

    In this paper, the first total synthesis of (+)-bucidarasins A and C is described. The chiral starting material was successfully obtained via reduction using a CBS catalyst and selective mono-TBS ether formation of trans -2-benzyloxymethyl-2-methylcyclohexane-1,3-diol, which was crucial to the successful enantioselective total synthesis of (+)-bucidarasins A and C. A synthetic approach towards (+)-bucidarasin C, based on the Barton-McCombie protocol, using V-70 as a radical promoter at low temperature to remove the C6-hydroxy moiety is also described.

    Original languageEnglish
    Pages (from-to)332-350
    Number of pages19
    JournalHeterocycles
    Volume91
    Issue number2
    DOIs
    Publication statusPublished - 2015

    Fingerprint

    Ether
    Catalysts
    Temperature
    bucidarasin A
    bucidarasin C
    methylcyclohexane
    V 70

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Organic Chemistry
    • Pharmacology

    Cite this

    Enantioselective total synthesis of (+)-bucidarasins A and C. / Usui, Kenji; Nakada, Masahisa.

    In: Heterocycles, Vol. 91, No. 2, 2015, p. 332-350.

    Research output: Contribution to journalArticle

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