Synthetic studies on (+)-bucidarasin C: Two diastereoselective transannular reactions producing cis-decaline derivatives that show reversal selectivity

Akinobu Nakahara, Misaki Kanbe, Masahisa Nakada

    Research output: Contribution to journalArticle

    6 Citations (Scopus)

    Abstract

    This manuscript describes studies on the construction of the cis-decaline core of (+)-bucidarasin C. The transannular Diels-Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis-decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis-decaline derivative as the major product.

    Original languageEnglish
    Pages (from-to)1518-1522
    Number of pages5
    JournalTetrahedron Letters
    Volume53
    Issue number12
    DOIs
    Publication statusPublished - 2012 Mar 21

    Fingerprint

    Lactones
    Derivatives
    Cycloaddition Reaction
    bucidarasin C

    Keywords

    • Bucidarasin
    • Cascade reaction
    • Diels-Alder reaction
    • Michael reaction
    • Stereoselective reaction
    • Transannular reaction

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Synthetic studies on (+)-bucidarasin C : Two diastereoselective transannular reactions producing cis-decaline derivatives that show reversal selectivity. / Nakahara, Akinobu; Kanbe, Misaki; Nakada, Masahisa.

    In: Tetrahedron Letters, Vol. 53, No. 12, 21.03.2012, p. 1518-1522.

    Research output: Contribution to journalArticle

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