(−)-Lyngbyaloside B, a Marine Macrolide Glycoside: Total Synthesis and Stereochemical Revision

H. Fuwa

    Research output: Chapter in Book/Report/Conference proceedingChapter

    1 Citation (Scopus)

    Abstract

    This account describes our endeavors on the total synthesis and structure elucidation of a marine macrolide glycoside, (−)-lyngbyaloside B. This natural product was isolated as a moderately cytotoxic constituent from the Palauan cyanobacterium Lyngbya sp. Our investigation started with the total synthesis of a nonnatural analog, (−)-13-demethyllyngbyaloside B, which was completed by exploiting an esterification/ring-closing metathesis strategy for the construction of the macrocyclic framework. Our efforts toward (−)-lyngbyaloside B were frustrated by the difficulties associated with the construction of the macrocycle involving an acylated tertiary alcohol. Eventually, the first total synthesis of the proposed structure of (−)-lyngbyaloside B was completed via an acyl ketene macrocyclization to forge the macrocyclic backbone. Because the proposed structure turned out to be erroneously assigned, we deduced the correct structure of (−)-lyngbyaloside B on the basis of the NMR data of the authentic material and molecular modeling. Ultimately, our revised structure was unambiguously verified through total synthesis.

    Original languageEnglish
    Title of host publicationStrategies and Tactics in Organic Synthesis
    PublisherAcademic Press Inc.
    Pages143-168
    Number of pages26
    DOIs
    Publication statusPublished - 2016 Jan 1

    Publication series

    NameStrategies and Tactics in Organic Synthesis
    Volume12
    ISSN (Print)1874-6004

    Keywords

    • Aldol reaction
    • Glycosylation
    • Macrolactonization
    • Macrolides
    • Stereochemical assignment

    ASJC Scopus subject areas

    • Drug Discovery
    • Organic Chemistry

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  • Cite this

    Fuwa, H. (2016). (−)-Lyngbyaloside B, a Marine Macrolide Glycoside: Total Synthesis and Stereochemical Revision. In Strategies and Tactics in Organic Synthesis (pp. 143-168). (Strategies and Tactics in Organic Synthesis; Vol. 12). Academic Press Inc.. https://doi.org/10.1016/B978-0-08-100756-3.00005-4