Enantioselective first total syntheses of the antiviral natural products xiamycins D and E.

Abstract

The enantioselective first total syntheses of marine pentacyclic indolosesquiterpenoids xiamycins D (4) and E (5) have been described for the first time to the best of our knowledge. The synthetic approach was designed to feature functionalization of enantiopure Wieland-Miescher ketone, Michael addition followed by Heck-type annulation/aromatization, regioselective sp3(C-H) activation, benzylic oxidation and diastereoselective reduction.