Biomimetic Enantioselective Total Synthesis of (-)-Petromindole.

The first enantioselective total synthesis of (-)-petromindole, an architecturally distinct congener of indole diterpene family, has been achieved. Key features of this synthetic route include the scalable and concise synthesis of tricyclic allylic alcohol from enantiopure Wieland-Mischer ketone derivative, and TMSOTf-mediated, highly efficient biomimetic C-4 cyclization of indole derivative for the rapid construction of a hexacyclic skeleton of petromindole.