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Streamlined Catalytic Asymmetric Synthesis of Atorvastatin

Authors

  • Yuji Kawato ,

    1. Institute of Microbial Chemistry, Tokyo (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan), Fax: (+81) 3-3441-8133
    2. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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  • Dr. Sandeep Chaudhary,

    1. Institute of Microbial Chemistry, Tokyo (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan), Fax: (+81) 3-3441-8133
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  • Dr. Naoya Kumagai,

    Corresponding author
    1. Institute of Microbial Chemistry, Tokyo (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan), Fax: (+81) 3-3441-8133
    • Institute of Microbial Chemistry, Tokyo (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan), Fax: (+81) 3-3441-8133
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  • Prof. Dr. Masakatsu Shibasaki 

    Corresponding author
    1. Institute of Microbial Chemistry, Tokyo (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan), Fax: (+81) 3-3441-8133
    2. JST, ACT-C, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
    • Institute of Microbial Chemistry, Tokyo (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan), Fax: (+81) 3-3441-8133
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Abstract

original image

An efficient enantioselective synthetic route to atorvastatin was developed based on a direct catalytic asymmetric aldol reaction. The expensive chiral ligand used in the initial aldol reaction was readily recovered (91 %) and reused. Implementation of an oxy-Michael reaction for the construction of the syn-1,3-diol unit eliminated several redundant steps, allowing for rapid access to the common intermediate in six steps (see scheme).

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