Enantioselective Total Synthesis of (−)-Stenine

Authors

  • Dr. Jingbo Chen,

    1. Key Laboratory of Medicinal Chemistry for Natural Resources (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091 (P. R. China)
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  • Jingchao Chen,

    1. Key Laboratory of Medicinal Chemistry for Natural Resources (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091 (P. R. China)
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  • Yan Xie,

    1. Key Laboratory of Medicinal Chemistry for Natural Resources (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091 (P. R. China)
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  • Prof. Dr. Hongbin Zhang

    Corresponding author
    1. Key Laboratory of Medicinal Chemistry for Natural Resources (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091 (P. R. China)
    • Key Laboratory of Medicinal Chemistry for Natural Resources (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091 (P. R. China)
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  • This work was supported by grants (20925205, 20562013, and 20832005) from the National Natural Science Foundation of China and a grant (973 program: 2009CB522304) from the National Basic Research Program of China. Dr. Xiaonian Li from the Kunming Institute of Botany is gratefully acknowledged for the X-ray crystallographic analysis of compound 19.

Abstract

original image

In control: (−)-Stenine has been synthesized in 14 steps from commercially available compounds with an overall yield of 5.9 % by using a method that is based on double Michael addition. In the key step, the stereogenic centers that are required for (−)-stenine are generated in a highly stereocontrolled, asymmetric, one-pot cyclization to give a densely substituted cyclohexane core.

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