General and efficient strategy for erythrinan and homoerythrinan alkaloids: syntheses of (+/-)-3-demethoxyerythratidinone and (+/-)-erysotramidine |
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Authors: | Gao Shuanhu Tu Yong Qiang Hu Xiangdong Wang Shaohua Hua Rongbao Jiang Yijun Zhao Yuming Fan Xiaohui Zhang Shuyu |
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Affiliation: | State Key Laboratory of Applied Organic Chemistry & Department of Chemistry, Lanzhou University, PRC. |
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Abstract: | [reaction: see text] A general and efficient strategy to both aromatic-type and nonaromatic-type erythrinan and homoerythrinan alkaloids has been developed. This approach involves a key two-step sequence, an alkylation of a ketone with various N-substituted iodoacetamides followed by a N-acyliminium ion promoted intramolecular cyclization, and represents one of the shortest routes to erythrinan and homoerythrinan alkaloids. As the application, the formal total synthesis of (+/-)-3-demethoxyerythratidinone and the total synthesis of (+/-)-erysotramidine have been achieved, respectively. |
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