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Biomimetic Total Synthesis of (+)-Gelsemine

Authors

  • Xuan Zhou,

    1. Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610041 (China)
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  • Tao Xiao,

    1. Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610041 (China)
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  • Yusuke Iwama,

    1. Graduate School of Phamaceutical Sciences, Tohoku University, Sendai, 980-8578 (Japan)
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  • Prof. Dr. Yong Qin

    Corresponding author
    1. Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610041 (China)
    2. Innovative Drug Research Centre and College of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 401331 (China)
    • Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610041 (China)
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  • We are grateful for financial supports from NSFC (20825207, 21021001, and 21132006), the National Basic Research Program of China (973 program, 2010CB833200), the State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, and Tohuku University Global COE Program and JSPS Predoctoral Fellowship for Y.I.

Abstract

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Challenging: (+)-gelsemine was synthesized from (R,R)-aziridine 1 in 25 steps with approximately 1 % overall yield. A multistep, one-pot enol–oxonium cyclization cascade was used to construct, simultaneously, the E ring, F ring, C3 stereocenter, and C7 quaternary stereocenter. This synthesis using the enol–oxonium cyclization reaction as a key step to make the cage structure has demonstrated the proposed biosynthetic pathway of the gelsemine family.

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