Asymmetric and highly stereoselective synthesis of the def-ring moiety of (-)-FR182877 and its derivative inducing mitotic arrest

Yu Kobayakawa, Yusuke Mori, Hideki Okajima, Yasuhiko Terada, Masahisa Nakada

    Research output: Contribution to journalArticle

    6 Citations (Scopus)

    Abstract

    The asymmetric and highly stereoselective synthesis of compound 1, which corresponds exactly to the DEF-ring moiety of (-)-FR182877, and the biological activities of its derivatives are described. All derivatives of 1 showed no activity in the tubulin polymerization assay, but one derivative was shown to have the ability to induce mitotic arrest by interfering with microtubule dynamics, and the cellular effects are similar to those of paclitaxel.

    Original languageEnglish
    Pages (from-to)2086-2089
    Number of pages4
    JournalOrganic Letters
    Volume14
    Issue number8
    DOIs
    Publication statusPublished - 2012 Apr 20

    Fingerprint

    Tubulin
    activity (biology)
    Paclitaxel
    Microtubules
    Polymerization
    polymerization
    Derivatives
    rings
    synthesis
    Bioactivity
    Assays
    FR 182877
    butyl phosphorotrithioate

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

    Cite this

    Asymmetric and highly stereoselective synthesis of the def-ring moiety of (-)-FR182877 and its derivative inducing mitotic arrest. / Kobayakawa, Yu; Mori, Yusuke; Okajima, Hideki; Terada, Yasuhiko; Nakada, Masahisa.

    In: Organic Letters, Vol. 14, No. 8, 20.04.2012, p. 2086-2089.

    Research output: Contribution to journalArticle

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