Chemistry

Indole test

Catalysis

Alkyne

Aromatization

Allylic rearrangement

Organic chemistry

Steric effects

Olefin fiber

Stereochemistry

Total synthesis

Stille reaction

Journal of the American Chemical Society

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.

Total Syntheses of Aflavazole and 14-Hydroxyaflavinine