Synthesis of Protected 2-Amino-8-oxo-9,10-epoxydecanoic Acid from 2-Aminosuberic Acid Derivatives

Article abstract of DOI:10.1021/jo00152a005

A method is reported for synthesizing derivatives of 2-amino-8-oxo-9,10-epoxydecanoic acid (Aoe) from 2-aminosuberic acid (Asu) derivatives under conditions that do not disrupt peptide bonds.The epoxy ketone amino acid Aoe is found in three biologically active cyclic peptides.Ethyl 2-(acetylamino)suberate was converted to ethyl 2-DL-(acetylamino)-8-oxo-(RS)-9,10-epoxydecanoate in 45-50 percent yield by sequential reactions with phosphorus pentachloride followed by reaction with tetravinyltin and benzylchlorobis(triphenylphosphine)palladium(II) to give the vinyl ketone in 70 percent yield.Epoxidation of enone with tert-butyl hydroperoxide using triton B as catalyst gave the N-acetyl ethyl ester of Aoe in 70 percent yield.Methods for preparing protected 2-aminosuberic acid derivatives from glycine ester benzal imine are also described.