Journal of Organic Chemistry p. 432 - 434 (1983)
Update date:2022-08-04
Topics:
Rich, Daniel H.
Singh, Jasbir
Gardner, Joseph H.
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.
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