An efficient and enantioselective total synthesis of naturally occurring L-783277

Hwan Geun Choi, Jung Beom Son, Dong Sik Park, Young Jin Ham, Jung Mi Hah, Taebo Sim

    Research output: Contribution to journalArticlepeer-review

    16 Citations (Scopus)

    Abstract

    Naturally occurring L-783277 which belongs to 14-membered resorcylic acid lactones (RALs) turned out to be a potent kinase inhibitor against MEK (MAP kinase kinase). We successfully accomplished efficient and enantioselective total synthesis of L-783277 based on convergent assembly of one aromatic unit and two chiral building blocks with efficient orthogonal protection-deprotection strategy. Three key steps composed of olefin cross metathesis, addition of acetylene derivative to aldehyde, and Yamaguchi macrolactonization were subsequently employed to construct the framework of L-783277. The optical rotation value of L-783277 is for the first time presented in this Letter.

    Original languageEnglish
    Pages (from-to)4942-4946
    Number of pages5
    JournalTetrahedron Letters
    Volume51
    Issue number38
    DOIs
    Publication statusPublished - 2010

    Bibliographical note

    Funding Information:
    This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MODHRD, KRF-2007-355-C00027).

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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