Dimeric indolosesquiterpene alkaloids typically N-N- and C-N-linked xiamycin dimers feature pentacyclic framework with four contiguous stereogenic centers at the periphery of a trans-decalin scaffold to which a carbazole unit is attached. In comparison with the actual biosynthetic dixiamycin derivatives, we designed the C-C-linked xiamycin dimers, aiming to serve as a powerful tool to create unique scaffold as drug candidates. In this work, we disclose the first synthetic route to access C-C dimeric indolosesquiterpene skeleton, featuring a hypervalent Iodine (PIFA) catalyzed oxidative dimerization reaction in a single-step operation with an overwhelming control of the chemoselectivity and regioselectivity. This strategy has been successfully applied to synthesis of C-C dimer of xiamycin A (3) and xiamycin A methyl ester (15), that demonstrates a new synthetic pathway for dimeric indolosesquiterpene alkaloids.

This article is Open Access

Please wait while we load your content... Something went wrong. Try again?