Synthetic studies on chartelline C: Stereoselective construction of the core skeleton

Kotaro Iwasaki, Rentaro Kanno, Toshiharu Morimoto, Tohru Yamashita, Satoshi Yokoshima, Tohru Fukuyama

    Research output: Contribution to journalArticlepeer-review

    12 Citations (Scopus)

    Abstract

    What a core-ker! The title synthesis was achieved using a route featuring an intramolecular Mitsunobu reaction of a nosyl amide, stereoselective construction of the β-lactam, and formation of an enamide moiety by selenoxide elimination. The stereochemistry of the alkylation for the formation of the β-lactam was controlled by a secondary hydroxy group on the ten-membered ring. SEM=2-(trimethylsilyl)ethoxymethyl; TBS=tert- butyldimethylsilyl.

    Original languageEnglish
    Pages (from-to)9160-9163
    Number of pages4
    JournalAngewandte Chemie - International Edition
    Volume51
    Issue number36
    DOIs
    Publication statusPublished - 2012 Sep 3

    Keywords

    • Mitsunobu reaction
    • imidazole
    • natural products
    • spiro β-lactams
    • total synthesis

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)

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