biostudies-literatureScott TZNational Institute of General Medical SciencesNIGMS NIH HHS2160-2164https://www.ebi.ac.uk/biostudies/studies/S-EPMC9204752biostudies-literatureUnknown24(11)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.Organic lettersTotal Synthesis and Stereochemical Assignment of (-)-Psychotridine.PMC9204752GM-141963R35 GM141963R01 GM089732GM-089732Armelin VFMovassaghi MScott TZfalseTotal 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.2022-01-01T00:00:00Z2022 Mar2025-04-05T11:20:13.951Z2025-04-05T11:20:13.951ZS-EPMC92047523529725510.1021/acs.orglett.2c00448