Enantioselective synthesis of SNAP-7941: chiral dihydropyrimidone inhibitor of MCH1-R.
J Org Chem
; 73(19): 7651-6, 2008 Oct 03.
Article
en En
| MEDLINE
| ID: mdl-18767801
An enantioselective synthesis of SNAP-7941, a potent melanin concentrating hormone receptor antagonist, was achieved by using two organocatalytic methods. The first method utilized to synthesize the enantioenriched dihydropyrimidone core was the Cinchona alkaloid-catalyzed Mannich reaction of beta-keto esters to acylimines and the second was the chiral phosphoric acid-catalyzed Biginelli reaction. Completion of the synthesis was accomplished via selective urea formation at the N3 position of the dihydropyrimidone with the 3-(4-phenylpiperidin-1-yl)propylamine side chain fragment. The synthesis of SNAP-7921 highlights the utility of asymmetric organocatalytic methods in the construction of an important class of chiral heterocycles.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Piperidinas
/
Pirimidinas
/
Pirimidinonas
/
Receptores de Somatostatina
Límite:
Humans
Idioma:
En
Revista:
J Org Chem
Año:
2008
Tipo del documento:
Article
País de afiliación:
Estados Unidos
Pais de publicación:
Estados Unidos