Synthetic studies on dragmacidin D: Synthesis and assembly of three fragments towards an advanced intermediate

Masato Oikawa, Minoru Ikoma, Makoto Sasaki

    Research output: Contribution to journalArticlepeer-review

    13 Citations (Scopus)

    Abstract

    We report herein the approach to the key advanced intermediate in the synthesis of the bioactive marine natural product dragmacidin D. By employing a modular synthesis strategy of three fragments (5, 7, and 8), the advanced intermediate 3 has been successfully synthesized in 2.5% yield over 15 steps by starting from nitrotoluene 20. The synthesis also involves sequential cross-coupling reactions, namely Sonogashira and Suzuki-Miyaura reactions, so that various analogues can be efficiently synthesized, which will allow the study of structure-activity relationships of dragmacidin D.

    Original languageEnglish
    Pages (from-to)4654-4666
    Number of pages13
    JournalEuropean Journal of Organic Chemistry
    Issue number24
    DOIs
    Publication statusPublished - 2011 Aug 1

    Keywords

    • Cross-coupling
    • Natural products
    • Nitrogen heterocycles
    • Synthesis design

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry
    • Organic Chemistry

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