An effective synthesis of (.+-.)-(E)-2-amino-5-phosphono-3-pentenoic acid by palladium (II)-assisted migration of the double bond.

Abstract

A new approach for the synthesis of (±)-(E)-2-amino-5-phosphono-3-pentenoic acid (E-APPA) is described. The key intermediate, (E)-5-acetoxy-3, 4-dehydronorvaline derivative 8, was prepared by [3, 3]-sigmatropic rearrangement of allyl acetate 7 in the presence of Pd(II) catalyst. The acetoxy group in 8 was transformed into the phosphonyl group to furnish (E)-APPA in a moderate yield.