1.
J Org Chem
; 73(8): 3212-7, 2008 Apr 18.
Article
in English
| MEDLINE
| ID: mdl-18348575
ABSTRACT
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.
Subject(s)
Cobalt/chemistry , Nitriles/chemistry , Aldehydes/chemical synthesis , Aldehydes/chemistry , Caprolactam/chemistry , Cyclization , Homoserine/chemical synthesis , Homoserine/chemistry , Isomerism , Methionine/chemistry , Molecular Structure , Oxidation-Reduction , Temperature
2.
J Org Chem
; 68(6): 2338-42, 2003 Mar 21.
Article
in English
| MEDLINE
| ID: mdl-12636400
ABSTRACT
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.
