Total synthesis, stereochemical reassignment, and biological evaluation of (-)-lyngbyaloside B

Haruhiko Fuwa, Yuta Okuaki, Naoya Yamagata, Makoto Sasaki

    Research output: Contribution to journalArticlepeer-review

    15 Citations (Scopus)

    Abstract

    (-)-Lyngbyaloside B is a 14-membered macrolide glycoside isolated from the marine cyanobacterium Lyngbya sp. as a cytotoxic substance by Moore and co-workers. The first total synthesis of (-)-lyngbyaloside B and the reassignment of its stereostructure is described. The synthesis features an Abiko-Masamune aldol reaction, a vinylogous Mukaiyama aldol reaction, and a macrocyclization involving an acyl ketene intermediate for the construction of the macrocyclic backbone, which contains an acylated tertiary alcohol. The antiproliferative activity of selected compounds against a small panel of human cancer cell lines is also reported.

    Original languageEnglish
    Pages (from-to)868-873
    Number of pages6
    JournalAngewandte Chemie - International Edition
    Volume54
    Issue number3
    DOIs
    Publication statusPublished - 2015 Jan 12

    Keywords

    • Aldol reactions
    • Macrolide glycosides
    • Natural products
    • Structure determination
    • Total synthesis

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)

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