Catalytic Asymmetric Total Synthesis of (-)-Actinophyllic Acid.
J Am Chem Soc
; 138(10): 3298-301, 2016 Mar 16.
Article
en En
| MEDLINE
| ID: mdl-26910382
ABSTRACT
Described herein is a catalytic asymmetric total synthesis of (-)-actinophyllic acid, with the key step being a chiral phosphine-catalyzed [3 + 2] annulation between an imine and an allenoate to form a pyrroline intermediate in 99% yield and 94% ee. The synthesis also features CuI-catalyzed coupling between a ketoester and a 2-iodoindole to shape the tetrahydroazocine ring; intramolecular alkylative lactonization; SmI2-mediated intramolecular pinacol coupling between ketone and lactone subunits to assemble the complex skeleton of (-)-actinophyllic acid; and an unprecedented regioselective dehydroxylation.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Alcaloides Indólicos
Idioma:
En
Revista:
J Am Chem Soc
Año:
2016
Tipo del documento:
Article
País de afiliación:
Estados Unidos