Total synthesis of 13-demethyllyngbyaloside B

Haruhiko Fuwa, Naoya Yamagata, Asami Saito, Makoto Sasaki

    Research output: Contribution to journalArticlepeer-review

    18 Citations (Scopus)

    Abstract

    Total synthesis of 13-demethyllyngbyaloside B, an unnatural analogue of a marine macrolide glycoside lyngbyaloside B, has been achieved. The 14-membered macrocyclic backbone was constructed in a convergent manner via esterification and ring-closing metathesis. The bromodiene side chain was introduced by means of a Stille-type reaction and a subsequent bromodesilylation. Finally, the rhamnopyranose unit was stereoselectively introduced by glycosylation under Schmidt conditions.

    Original languageEnglish
    Pages (from-to)1630-1633
    Number of pages4
    JournalOrganic letters
    Volume15
    Issue number7
    DOIs
    Publication statusPublished - 2013 Apr 5

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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