Total Synthesis of (+)-Isolysergol.
J Org Chem
; 88(13): 8761-8769, 2023 Jul 07.
Article
em En
| MEDLINE
| ID: mdl-37276259
ABSTRACT
The enantioselective synthesis of (+)-isolysergol was completed in 18 steps, and an overall yield of 11% was obtained from (2R)-(+)-phenyloxirane as a chiral pool. Key features of the synthesis include a stereoselective intramolecular 1,3-dipolar addition of nitrone with terminal olefin and a Cope elimination to furnish the D ring. A rhodium-catalyzed intramolecular [3 + 2] annulation of a benzene ring with α-imino carbenoid was designed to afford the 3,4-fused indole scaffold at the late stage of the synthesis.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Ergolinas
Idioma:
En
Ano de publicação:
2023
Tipo de documento:
Article