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

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 rin...

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Bibliographic Details
Main Authors: Robinson, J, Lee, V, Claridge, T, Baldwin, J, Schofield, C
Format: Journal article
Language:English
Published: 1998
Description
Summary: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 NAN 3, followed by deprotection to give aminohydroxy prolines.