Stereoselective synthesis of the C17–C29 fragment of amphidinolide N

Yuki Fujishima, Yusuke Ogura, Ryo Towada, Masaru Enomoto, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    8 Citations (Scopus)

    Abstract

    An enantio- and diastereoselective synthesis of the C17–C29 fragment of amphidinolide N, an extremely potent macrocyclic cytotoxin of marine origin, has been accomplished from a known olefinic ester by a 10-step sequence that involves a ring opening of a chiral epoxide with a dithiane derivative to construct the full carbon skeleton, a highly diastereoselective reduction of a β-hydroxy ketone intermediate to install the C21 asymmetric center, and a one-pot Sharpless AD/cyclization sequence to form a trans-substituted tetrahydrofuran ring system.

    Original languageEnglish
    Pages (from-to)5240-5242
    Number of pages3
    JournalTetrahedron Letters
    Volume57
    Issue number47
    DOIs
    Publication statusPublished - 2016

    Keywords

    • Amphidinolide
    • Cytotoxic
    • Macrolide
    • Partial synthesis
    • Polyketide

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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