期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 2, 页码 967-976出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02918
关键词
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资金
- National Science Foundation of China (NSFC) [21672181/21272199]
- Research Grants Council (Hong Kong) (RGC) [CUHK14309216/CUHK14303815/403012]
- NSFC/RGC Joint Research Scheme [N_CUHK451/13]
- Shenzhen Science and Technology Innovation Committee [JCYJ20160608151520697]
- Ministry of Science and Technology (China)
- Innovation and Technology Commission's Guangdong-Hong Kong Technology Cooperation Funding Scheme [GHP/004/16GD]
- Chinese Academy of Sciences-Croucher Foundation
- Chinese University of Hong Kong [4053325]
The total syntheses of Aspidosperma and Kopsia alkaloids (-)-deoxoapodine, (-)-kopsifoline D, and (-)-beninine are described through a domino deprotection-Michael addition-nucleophilic substitution protocol to assemble the core framework in efficient steps. Corey-Bakshi-Shibata reduction was employed to afford the enantioenriched intermediate for the total syntheses of the aforementioned alkaloids. The chirality was shown to completely transfer to the backbone using Johnson-Claisen rearrangement. The enantioselective total syntheses of (-)-kopsifoline D and (-)-beninine were accomplished for the first time. Our strategy opens up practical avenues for the total synthesis of structurally similar alkaloids.
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