Synthesis of (2S, 3R, 4S), (2S, 3S, 4R)-epoxyprolines and aminohydroxyprolines

Article abstract of DOI:10.1016/S0040-4020(97)10352-0

25, 3R, 4S- and 25, 38, 4R-epoxy-L-prolines were synthesised from trans- 4-hydroxy-L-proline. Assignment of the stereochemical configurations of the epoxy prolines was achieved by n.O.e. studies and chemical correlation. The synthetic utility of the protected epoxides was investigated briefly by ring opening with NAN₃, followed by deprotection to give aminohydroxy prolines.