Synthetic Studies Towards Crinine-Type Amaryllidaceae Alkaloids: Synthesis of (±)-Oxocrinine and Formal Synthesis of (±)-Crinine

被引:11
|
作者
Yang, Lijuan [2 ,3 ]
Wang, Xuequan [1 ]
Pan, Zhiqiang [1 ]
Zhou, Ming [1 ]
Chen, Wen [2 ,3 ]
Yang, Xiaodong [1 ]
机构
[1] Yunnan Univ, Key Lab Med Chem Nat Resource, Minist Educ, Sch Chem Sci & Technol, Kunming 650091, Yunnan, Peoples R China
[2] Yunnan Univ Nationalities, Key Lab Ethn Med Resource Chem, State Ethn Affairs Commiss, Kunming 650031, Yunnan, Peoples R China
[3] Minist Educ, Kunming 650031, Yunnan, Peoples R China
基金
中国国家自然科学基金;
关键词
Amaryllidaceae alkaloids; crinine; oxocrinine; total synthesis; quaternary carbon; AZA-COPE REARRANGEMENTS; CONCISE TOTAL-SYNTHESIS; DIELS-ALDER REACTION; SCELETIUM ALKALOIDS; ANTIMALARIAL ACTIVITY; LYCORINE;
D O I
10.1055/s-0030-1259288
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A flexible strategy leading to the synthesis of crinine-type Amaryllidaceae alkaloids, (+/-)-oxocrinine and (+/-)-crinine, has been developed. A notable feature in this synthetic route is the construction of tetrahydro-1H-benzo[c]azepine framework using an intramolecular Heck reaction and the formation of the sterically congested spiro cyclohexenone intermediate with a Robinson annulation.
引用
收藏
页码:207 / 210
页数:4
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