Total Synthesis and Stereochemical Assignment of (-)-Psychotridine.

ABSTRACT: 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.

SUBMITTER: Scott TZ 

PROVIDER: S-EPMC9204752 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature