1.
Org Lett
; 16(16): 4142-5, 2014 Aug 15.
Artículo
en Inglés
| MEDLINE
| ID: mdl-25084526
RESUMEN
An efficient enantioselective synthesis of the chiral polycyclic cholesteryl ester transfer protein (CETP) inhibitor 1 has been developed. The synthesis was rendered practical for large scale via the development of a modified Hantzsch-type reaction to prepare the sterically hindered pyridine ring, enantioselective hydrogenation of hindered ketone 6 utilizing novel BIBOP-amino-pyridine derived Ru complex, efficient ICl promoted lactone formation, and a BF3 mediated hydrogenation process for diastereoselective lactol reduction. This efficient route was successfully scaled to produce multikilogram quantities of challenging CETP drug candidate 1.
Asunto(s)
Proteínas de Transferencia de Ésteres de Colesterol/antagonistas & inhibidores , Piridinas/síntesis química , Piridinas/farmacología , Cristalografía por Rayos X , Hidrogenación , Conformación Molecular , Estructura Molecular , Piridinas/química , Estereoisomerismo
2.
Chemistry
; 18(6): 1577-81, 2012 Feb 06.
Artículo
en Inglés
| MEDLINE
| ID: mdl-22238176