Citation: Wang Huijing, Dong Qiuyan, Xie Qinxia, Tang Pei. Asymmetric synthesis of ABC tricyclic systems in Daphniphyllum alkaloid[J]. Chinese Chemical Letters, ;2020, 31(3): 685-688. doi: 10.1016/j.cclet.2019.08.033 shu

Asymmetric synthesis of ABC tricyclic systems in Daphniphyllum alkaloid

Wang Huijing ^a,c ,
Dong Qiuyan ^b ,
Xie Qinxia ^b ,
Tang Pei ^a,*,

a.
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China
b.
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China
c.
Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla 92093-0934, United States

peitang@scu.edu.cn

Received Date: 17 July 2019
Revised Date: 2 August 2019
Accepted Date: 21 August 2019
Available Online: 21 August 2019

Figures(4)

Efficient synthetic routs for the direct and rapid construction of [5-6-6] ABC tricyclic systems of daphmanidin A-type and calyciphylline A-type alkaloids have been successfully developed. For the daphmanidin A-type, the synthesis of [5-6-6] tricyclic framework utilize a HCl-mediated intramolecular Aldol reaction to construct the bicyclo[2.2.2]octane core and a thermal condensation to afford the ABC ring system. In addition, for the calyciphylline A-type, an improved synthesis of ABC [5-6-6] tricyclic system was developed, featuring an introduction of methyl ester group at C2 before the Pd-catalyzed intramolecular oxidative alkylation to construct the desired bowl-shape tricyclic core with stereochemical control.
- Daphniphyllum alkaloid,
- Calyciohylline N,
- 21-Deoxymacropodumine D,
- ABC tricyclic framework,
- Intramolecular Aldol reaction,
- Pd-catalyzed intramolecular oxidative,
- alkylation
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