Total Synthesis and Stereochemical Assignment of (-)-Psychotridine.
Org Lett
; 24(11): 2160-2164, 2022 03 25.
Article
in En
| MEDLINE
| ID: mdl-35297255
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.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Alkaloids
/
Indoles
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2022
Document type:
Article
Affiliation country:
United States