1.
J Org Chem
; 73(8): 3212-7, 2008 Apr 18.
Artigo
em Inglês
| MEDLINE
| ID: mdl-18348575
RESUMO
An expedient, five step synthesis of caprolactam 1 is reported starting from natural L-homoserine. The key step is a chemoselective reductive cyclization of alpha,beta-unsaturated nitrile 10 mediated by Raney-Co type metals. This hydrogenation is extensively investigated in order to account for the observed product distribution and yields.
Assuntos
Cobalto/química , Nitrilas/química , Aldeídos/síntese química , Aldeídos/química , Caprolactama/química , Ciclização , Homosserina/síntese química , Homosserina/química , Isomerismo , Metionina/química , Estrutura Molecular , Oxirredução , Temperatura
2.
J Org Chem
; 68(6): 2338-42, 2003 Mar 21.
Artigo
em Inglês
| MEDLINE
| ID: mdl-12636400
RESUMO
A convergent synthesis was developed for the production of the core structure of prostaglandin D(2) receptor antagonists for the treatment of allergic rhinitis. The key steps in this synthesis were a highly diastereoselective alkylation of (+)-nopinone, a chemo- and stereoselective reduction of an oxime to an amine, and a well-controlled reduction of an aminoalkyne to a (Z)-olefin.
