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Structure Elucidation and Enantioselective Total Synthesis of the Potent HMG-CoA Reductase Inhibitor FR901512 via Catalytic Asymmetric Nozaki−Hiyama Reactions

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    Structure Elucidation and Enantioselective Total Synthesis of the Potent HMG-CoA Reductase Inhibitor FR901512 via Catalytic Asymmetric Nozaki−Hiyama Reactions
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    Department of Chemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2007, 129, 14, 4164–4165
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    https://doi.org/10.1021/ja070812w
    Published March 17, 2007
    Copyright © 2007 American Chemical Society
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    Abstract

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    The structure elucidation and enantioselective total synthesis of the potent HMG-CoA reductase inhibitor FR901512 were accomplished. FR901512 was prepared in 15 steps from the commercially available 2-bromo-4-methylbenzaldehyde via FR901516 in 16.3% overall yield (89% average yield). The catalytic asymmetric Nozaki−Hiyama reactions developed by us proved their applicability and reliability through this work, enabling the concise, efficient, and protecting-group-free enantioselective total syntheses of these new statins.

    Copyright © 2007 American Chemical Society

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    Cited By

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    This article is cited by 36 publications.

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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2007, 129, 14, 4164–4165
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja070812w
    Published March 17, 2007
    Copyright © 2007 American Chemical Society
    Request reuse permissions

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