An efficient asymmetric synthesis of an estrogen receptor modulator by sulfoxide-directed borane reduction.
Proc Natl Acad Sci U S A
; 101(16): 5776-81, 2004 Apr 20.
Article
en En
| MEDLINE
| ID: mdl-15079059
ABSTRACT
An efficient asymmetric synthesis of a selective estrogen receptor modulator (SERM) that has a dihydrobenzoxathiin core structure bearing two stereogenic centers is reported. The stereogenic centers were established by an unprecedented chiral sulfoxide-directed stereospecific reduction of an alpha,beta-unsaturated sulfoxide to the saturated sulfide in one step. Studies to elucidate the mechanism for this reduction are reported. Highly efficient Cu(I)-mediated ether formation was used to install the ether side chain, and selective debenzylation conditions were developed to remove the benzyl protecting groups on the phenols.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Safrol
/
Boranos
/
Moduladores de los Receptores de Estrógeno
Idioma:
En
Revista:
Proc Natl Acad Sci U S A
Año:
2004
Tipo del documento:
Article
País de afiliación:
Estados Unidos