Total synthesis of (-)-FR182877 through tandem IMDA-IMHDA reactions and stereoselective transition-metal-mediated transformations

Natsumi Tanaka, Takahiro Suzuki, Takehiko Matsumura, Yosuke Hosoya, Masahisa Nakada

    Research output: Contribution to journalArticle

    32 Citations (Scopus)

    Abstract

    Intelligent design: The total synthesis of the cytotoxic (-)- FR182877 relies on 1) tandem Diels-Alder reactions to close rings A-D (see scheme), 2) a palladium-mediated 7- exo-trig reaction, and 3) an iridium-mediated isomerization followed by epimerization and stereoselective reduction.

    Original languageEnglish
    Pages (from-to)2580-2583
    Number of pages4
    JournalAngewandte Chemie - International Edition
    Volume48
    Issue number14
    DOIs
    Publication statusPublished - 2009 Mar 23

    Fingerprint

    Religious Philosophies
    Iridium
    Cycloaddition Reaction
    Palladium
    Isomerization
    Transition metals
    Metals
    FR 182877

    Keywords

    • Antitumor Agents
    • Cycloaddition
    • Natural products
    • Polycycles
    • Strained molecules

    ASJC Scopus subject areas

    • Chemistry(all)
    • Catalysis
    • Medicine(all)

    Cite this

    Total synthesis of (-)-FR182877 through tandem IMDA-IMHDA reactions and stereoselective transition-metal-mediated transformations. / Tanaka, Natsumi; Suzuki, Takahiro; Matsumura, Takehiko; Hosoya, Yosuke; Nakada, Masahisa.

    In: Angewandte Chemie - International Edition, Vol. 48, No. 14, 23.03.2009, p. 2580-2583.

    Research output: Contribution to journalArticle

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