Total Syntheses of Aflavazole and 14-Hydroxyaflavinine

详细信息    查看全文

• 作者：Hailong Li ; Qifeng Chen ; Zhaohong Lu ; Ang Li
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：December 7, 2016
• 年：2016
• 卷：138
• 期：48
• 页码：15555-15558
• 全文大小：486K
• ISSN：1520-5126

文摘

The first total syntheses of aflavazole (6) and 14-hydroxyaflavinine (8), two sterically congested indole diterpenoids, were accomplished. AlI₃-promoted alkyne Prins cyclization was exploited to construct their key structural motifs. An electrocyclization–aromatization sequence assembled the pentasubstituted arene of 6, and a Stille–Migita coupling furnished the tetrasubstituted olefin of 8. The benzylic and allylic C–O bonds were reductively cleaved at the late stage of the syntheses, respectively.