Total Syntheses of Aflavazole and 14-Hydroxyaflavinine

• DOI: 10.1021/jacs.6b10880
• Publication Date: 2016-11-16T15:26:56Z
• Authors: Hailong Li; Qifeng Chen; Zhaohong Lu; Ang Li
• Keywords: Stille reaction; Alkyne; Aromatization

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 6, a Stille-Migita coupling furnished tetrasubstituted olefin 8. benzylic allylic C-O bonds reductively cleaved at late stage syntheses, respectively.