Structure elucidation and enantioselective total synthesis of the HMG-CoA reductase inhibitors FR901512 and FR901516

Masahiro Inoue, Masahisa Nakada

    Research output: Contribution to journalArticle

    2 Citations (Scopus)

    Abstract

    The enantioselective total synthesis of the potent HMGCoA reductase inhibitors FR901512 (1) and FR901516 (2) is reviewed. FR901512 was prepared in 15 steps from commercially available compound via 2 in 16.3% overall yield (89% average yield). This study validated the applicability and reliability of the catalytic asymmetric Nozaki-Hiyama reactions that were developed by us. These reactions enabled the concise, efficient, and protecting-group-free enantioselective total syntheses of these new statins.

    Original languageEnglish
    Pages (from-to)3694-3707
    Number of pages14
    JournalSynthesis
    Issue number21
    DOIs
    Publication statusPublished - 2009

    Fingerprint

    Hydroxymethylglutaryl-CoA Reductase Inhibitors
    Oxidoreductases
    FR901512

    Keywords

    • Asymmetric catalysis
    • Enantioselective synthesis
    • Nozaki-Hiyama reaction
    • Structure elucidation
    • Total synthesis

    ASJC Scopus subject areas

    • Organic Chemistry
    • Catalysis

    Cite this

    Structure elucidation and enantioselective total synthesis of the HMG-CoA reductase inhibitors FR901512 and FR901516. / Inoue, Masahiro; Nakada, Masahisa.

    In: Synthesis, No. 21, 2009, p. 3694-3707.

    Research output: Contribution to journalArticle

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