Stereoselective Synthesis of 7-epi-Incarvilline

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• 作者：Hyowon Seo ; Hwayoung Yun ; Sujin Lee ; Jaebong Jang ; Young Taek Han ; Dae-Duk Kim ; Jeeyeon Lee ; Young-Ger Suh
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：February 1, 2013
• 年：2013
• 卷：15
• 期：3
• 页码：531-533
• 全文大小：249K
• 年卷期：v.15,no.3(February 1, 2013)
• ISSN：1523-7052

文摘

The enantioselective synthesis of 7-epi-incarvilline for formal syntheses of (鈭?-incarvilline, (+)-incarvine C, and (鈭?-incarvillateine is described. The key features of our synthesis involve (1) stereoselective construction of the optically active bicyclic lactone utilizing Pd(0)-catalyzed allylic alkylation, (2) efficient transformation of the bridged bicyclic lactone to the key bicyclic lactam skeleton, and (3) stereoselective elaborations of two stereocenters via a substrate-controlled catalytic hydrogenation and a 1,4-addition.