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Efficient Asymmetric Synthesis of a Bicyclic Amino Acid as a Core Structure of Telaprevir

Authors

  • Dr. Seiji Shirakawa,

    1. Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041
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  • Dr. Yan Liu,

    1. Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041
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  • Asuka Usui,

    1. Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041
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  • Prof. Dr. Keiji Maruoka

    Corresponding author
    1. Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041
    • Laboratory of Synthetic Organic Chemistry and Special Laboratory of Organocatalytic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan), Fax: (+81) 75-753-4041
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Abstract

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Telaprevir building block: Efficient asymmetric synthesis of bicyclic amino acid as a core structure of telaprevir has been accomplished via phase-transfer catalyzed stereoselective conjugate addition of glycine derivative to cyclopent-1-enecarbaldehyde. This synthetic method can be applied to the asymmetric synthesis of 3-substituted prolines.

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