Formal total synthesis of (-)-taxol

Masayuki Utsugi, Mitsuhiro Iwamoto, Sho Hirai, Hatsuo Kawada, Masahisa Nakada

    Research output: Contribution to journalArticle

    Abstract

    Formal total synthesis of (-)- taxol is described herein. This convergent synthesis was accomplished by utilizing two chiral fragments, both of which were prepared via asymmetric catalysis. A palladium-catalyzed reaction was found to afford the eight-membered ring effectively, i.e., a B-alkyl Suzuki-Miyaura coupling reaction and an intramolecular alkenylation of a methyl ketone successfully constructed the B-ring of taxol in excellent yield. During the preparation of a substrate for the palladium-catalyzed reaction, a unique rearrangement of the epoxy benzyl ether, via a 1, 5-hydride shift that generates the C3 stereogenic center and subsequently forms the C1-C2 benzylidene moiety, was observed. Strenuous efforts were required for transformations after the construction of the taxane scaffold to achieve the formal total synthesis of taxol because very few approaches are available for the synthesis of the target compound.

    Original languageEnglish
    Pages (from-to)1102-1114
    Number of pages13
    JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
    Volume75
    Issue number11
    DOIs
    Publication statusPublished - 2017 Jan 1

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    Paclitaxel
    Palladium
    Alkenylation
    Ketones
    Scaffolds
    Hydrides
    Ether
    Catalysis
    Substrates

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Formal total synthesis of (-)-taxol. / Utsugi, Masayuki; Iwamoto, Mitsuhiro; Hirai, Sho; Kawada, Hatsuo; Nakada, Masahisa.

    In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 75, No. 11, 01.01.2017, p. 1102-1114.

    Research output: Contribution to journalArticle

    Utsugi, Masayuki ; Iwamoto, Mitsuhiro ; Hirai, Sho ; Kawada, Hatsuo ; Nakada, Masahisa. / Formal total synthesis of (-)-taxol. In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry. 2017 ; Vol. 75, No. 11. pp. 1102-1114.
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