Stereocontrolled synthesis of psi[CH = CH] dipeptide isosteres.
A new stereocontrolled synthesis of the psi[CH = CH] dipeptide isostere is described. They key step of the sequence relies on the stereospecific alpha-alkylation of delta-amino-gamma-mesyloxy-alpha,beta-unsaturated esters. The broad availability of nucleophilic alpha-side chains by this method allows the preparation of a wide variety of psi[CH = CH] isosteres with predictable stereochemistry.
Kempf
D J
DJ
Pharmaceutical Products Division, Abbott Laboratories, Abbott Park, IL.
Wang
X C
XC
Spanton
S G
SG
D000478:Alkylation; D004151:Dipeptides / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D008958:Models, Molecular; D013237:Stereoisomerism
D004151:Dipeptides; D004952:Esters