期刊
ORGANIC LETTERS
卷 22, 期 19, 页码 7526-7530出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02720
关键词
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资金
- National Natural Science Foundation of China [21532003, 21871152, 21790332]
- 111 project of the Ministry of Education of China [B06005]
- Fundamental Research Funds for the Central Universities (Nankai University) [020-63191746]
Herein we report the first enantioselective total syntheses of pentacyclic homoproaporphine alkaloids by means of a route, which includes a tandem retro-oxa-Michael addition and nucleophilic substitution to generate the oxa-benzobicyclco[3.3.1]nonane core structure, a Pictet-Spengler cyclization to construct the fused B and C rings, and sequential Baeyer-Villiger oxidation and pinacol-type cyclization to install the hydroxyl-lactol moiety of D ring. With this unified route, six pentacyclic homoproaporphine alkaloids have been synthesized enantioselectively.
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