Catalytic Asymmetric Formal Total Synthesis of (2)-Triptophenolide and (+)-Triptolide

doi:10.1007/s13659-016-0100-z

Natural Products and Bioprospecting

2016, Vol. 6

Issue (3) : 183-186 DOI: 10.1007/s13659-016-0100-z

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Catalytic Asymmetric Formal Total Synthesis of (2)-Triptophenolide and (+)-Triptolide

Wen-Dan Xu^1,2, Liang-Qun Li^1,2, Ming-Ming Li³, Hui-Chun Geng^1,2, Hong-Bo Qin¹

1. State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, People's Republic of China;
2. University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3. Yunnan Baiyao Group Corporation Limited, Kunming 650032, People's Republic of China

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Abstract Catalytic asymmetric formal synthesis of (-)-Triptophenolide and (+)-Triptolide have been achieved. Key reaction involves Palladium catalyzed asymmetric conjugate addition of aryl boronic acid to 3-methyl cyclohexe-1-none to form quaternary carbon. Claisen rearrangement and subsequent aldol reaction furnished trans-decaline key intermediate, which assured a formal total synthesis of (-)-Triptophenolide and (+)-Triptolide.

Keywords Total synthesis Catalytic asymmetric Triptophenolide Triptolide

Fund:The manuscript was written through contributions of all authors

Issue Date: 08 February 2018

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Wen-Dan Xu,Liang-Qun Li,Ming-Ming Li, et al. Catalytic Asymmetric Formal Total Synthesis of (2)-Triptophenolide and (+)-Triptolide[J]. Natural Products and Bioprospecting, 2016, 6(3): 183-186.

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http://npb.kib.ac.cn/EN/10.1007/s13659-016-0100-z OR http://npb.kib.ac.cn/EN/Y2016/V6/I3/183

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