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Stereocontrolled synthesis of psi[CH = CH] dipeptide isosteres
D J Kempf1, X C Wang, S G Spanton
1Pharmaceutical Products Division, Abbott Laboratories, Abbott Park, IL.
International Journal of Peptide and Protein Research
|September 1, 1991
Abstract:
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.