Enantioselective total synthesis of (-)-FR182877

Natsumi Tanaka Suzuki, Takahiro Suzuki, Takehiko Matsumura, Yousuke Hosoya, Tomoyuki Nakazato, Masahisa Nakada

    Research output: Contribution to journalArticle

    1 Citation (Scopus)

    Abstract

    An enantioselective total syntfiesis of (-)-FR182877 is described. This total synthesis features 1) the one-pot stereoselective tandem IMDA-IMHDA reaction which affords the tetracyclic compound including the ABCD ring system of (-)-FR182877 with the correct new seven stereogenie centers, 2) the palladium-mediated 7-exo-trig intramolecular Heck reaction for the construction of the highly strained seven-membefed F-ring, and 3) the iridium-mediated isomerization of the allylic alcohol to the a-methyl ketone followed by epimerization and the stereoselective reduction to furnish all the stereogenic centers of (-)-FR182877.

    Original languageEnglish
    Pages (from-to)646-660
    Number of pages15
    JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
    Volume69
    Issue number6
    DOIs
    Publication statusPublished - 2011 Jun

    Fingerprint

    Iridium
    Palladium
    Isomerization
    Ketones
    FR 182877
    allyl alcohol

    Keywords

    • Anti-tumor cell compound
    • Enantioselective total synthesis
    • Intramolecular diels-alder (IMDA) reaction
    • Intramolecular Heck reaction
    • Intramolecular hetero diels-alder (IMHDA) reaction
    • Isomerisation reaction
    • Strained compound
    • Tandem IMDA-IMHDA reaction

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Enantioselective total synthesis of (-)-FR182877. / Suzuki, Natsumi Tanaka; Suzuki, Takahiro; Matsumura, Takehiko; Hosoya, Yousuke; Nakazato, Tomoyuki; Nakada, Masahisa.

    In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 69, No. 6, 06.2011, p. 646-660.

    Research output: Contribution to journalArticle

    Suzuki, Natsumi Tanaka ; Suzuki, Takahiro ; Matsumura, Takehiko ; Hosoya, Yousuke ; Nakazato, Tomoyuki ; Nakada, Masahisa. / Enantioselective total synthesis of (-)-FR182877. In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry. 2011 ; Vol. 69, No. 6. pp. 646-660.
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    AU - Hosoya, Yousuke

    AU - Nakazato, Tomoyuki

    AU - Nakada, Masahisa

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