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

• Short communication • Previous Articles

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

Received:2016-03-13 Revised:2016-04-11 Online:2018-02-08 Published:2016-06-24
Supported by:
The manuscript was written through contributions of all authors

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

通讯作者: Hong-Bo Qin,e-mail:qinhongbo@mail.kib.ac.cn
基金资助:
The manuscript was written through contributions of all authors

Abstract

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.

Key words: Total synthesis, Catalytic asymmetric, Triptophenolide, Triptolide

摘要： 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.

关键词: Total synthesis, Catalytic asymmetric, Triptophenolide, Triptolide

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

Wen-Dan Xu, Liang-Qun Li, Ming-Ming Li, Hui-Chun Geng, Hong-Bo Qin. Catalytic Asymmetric Formal Total Synthesis of (2)-Triptophenolide and (+)-Triptolide[J]. 应用天然产物, 2016, 6(3): 183-186.

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

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

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