Total synthesis of the proposed structure of didemnaketal B

Haruhiko Fuwa, Kumiko Sekine, Makoto Sasaki

    Research output: Contribution to journalArticlepeer-review

    14 Citations (Scopus)

    Abstract

    Total synthesis of the proposed structure of didemnaketal B has been accomplished. The C7-C21 spiroacetal domain was synthesized by exploiting our Suzuki-Miyaura coupling/spiroacetalization strategy. The C1-C7 acyclic domain was constructed via an Evans syn-aldol reaction and a vinylogous Mukaiyama aldol reaction. Finally, the C22-C28 side chain was introduced by means of a Nozaki-Hiyama-Kishi reaction. Comparison of the NMR spectroscopic data of our synthetic material with those of the authentic sample revealed that the proposed structure requires stereochemical reassignment.

    Original languageEnglish
    Pages (from-to)3970-3973
    Number of pages4
    JournalOrganic letters
    Volume15
    Issue number15
    DOIs
    Publication statusPublished - 2013 Aug 2

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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