Stereochemical assignment of topsentolide C2 by stereodivergent synthesis of its four diastereomers

Ryo Towada, Yusuke Kurashina, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    9 Citations (Scopus)

    Abstract

    Four diastereomers of topsentolide C2, a cytotoxic 9-membered lactone isolated from the marine sponge Topsentia sp., were synthesized stereodivergently from a common chiral seco acid by the combined use of the Yamaguchi and Mitsunobu lactonizations. Comparison of the NMR spectra of the four diastereomers with those of an authentic sample of topsentolide C2 led to the stereochemical determination of topsentolide C2 as 8R, 11S and 12S.

    Original languageEnglish
    Pages (from-to)6878-6881
    Number of pages4
    JournalTetrahedron Letters
    Volume54
    Issue number50
    DOIs
    Publication statusPublished - 2013 Dec 11

    Keywords

    • Cytotoxic
    • Lactonization
    • Oxylipin
    • Topsentolide
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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