Total Synthesis and Stereochemical Assignment of (-)-Psychotridine

We report the first enantioselective total synthesis and stereochemical assignment of (-)-psychotridine. The application of our diazene-directed assembly of enantiomerically enriched cyclotryptamines afforded a highly convergent synthesis of the pentameric alkaloid, allowing its detailed structural assignment. Highlights of the synthesis include the introduction of four quaternary stereocenters with complete stereochemical control in a single step via the photoextrusion of three molecules of dinitrogen from an advanced intermediate and metal-catalyzed C-H amination reactions in challenging settings.

Automated summary

This paper reports the first enantioselective total synthesis and stereochemical assignment of (-)-psychotridine. The highly convergent synthesis of the pentameric alkaloid was achieved through the application of diazene-directed assembly of enantiomerically enriched cyclotryptamines, allowing for detailed structural assignment. Notable highlights of the synthesis include the introduction of four quaternary stereocenters with complete stereochemical control in a single step via photoextrusion and metal-catalyzed C-H amination reactions under challenging conditions.