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Enantioselective Palladium-Catalyzed Decarboxylative Allylation of Carbazolones: Total Synthesis of (−)-Aspidospermidine and (+)-Kopsihainanine A

Authors

  • Zeqian Li,

    1. Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091 (China)
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    • These authors contributed equally to this work.

  • Shaoxiong Zhang,

    1. Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091 (China)
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    • These authors contributed equally to this work.

  • Shoutao Wu,

    1. Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091 (China)
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    • These authors contributed equally to this work.

  • Xiaolei Shen,

    1. Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091 (China)
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  • Liwei Zou,

    1. Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091 (China)
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  • Fengqun Wang,

    1. Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091 (China)
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  • Xiang Li,

    1. Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091 (China)
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  • Fangzhi Peng,

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

    1. Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091 (China)
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  • Prof. Zhihui Shao

    Corresponding author
    1. Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091 (China)
    • Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091 (China)
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  • We gratefully acknowledge financial support from the NSFC (20962023, 21162034, 20832005), the Program for New Century Excellent Talents in University (NCET-10-0907), and Yunnan government (2012FB114). We sincerely thank Prof. Yong Tang and Shuli You at Shanghai Institute of Organic Chemistry, CAS, and Prof. Yonggui Zhou at Dalian Institute of Chemical Physics, CAS, for valuable discussions. We also thank Prof. Kun Gao at Lanzhou University for providing us with the spectrum of the natural sample of kopsihainanine A.

Abstract

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Functionalized chiral carbazolones with α-quaternary carbon centers are formed through the ligand-controlled Pd-catalyzed enantioselective decarboxylative allylic alkylation of carbazolones (see scheme). This catalytic asymmetric reaction was employed as the key step in the total synthesis of aspidospermidine and (+)-kopsihainanine A.

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