Total Synthesis of (+)-Chimonanthine, (+)-Folicanthine, and (鈭?-Calycanthine

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• 作者：Ming Ding ; Kangjiang Liang ; Rui Pan ; Hongbin Zhang ; Chengfeng Xia
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：October 16, 2015
• 年：2015
• 卷：80
• 期：20
• 页码：10309-10316
• 全文大小：517K
• ISSN：1520-6904

文摘

Facile, straightforward, and asymmetric total syntheses of (+)-chimonanthine (1), (+)-folicanthine (2), and (鈭?-calycanthine (3) were accomplished in four to five steps from commercially available tryptamine. The synthesis features copper-mediated asymmetric cyclodimerization of chiral tryptamine derivative, which established a new entry into constructing the sterically hindered vicinal quaternary stereogenic carbon centers of dimeric hexahydropyrroloindole alkaloids in one procedure. An unprecedented base-induced isomerization from the chimonanthine skeleton to the calycanthine skeleton was observed and facilitated the synthesis of (鈭?-calycanthine (3).