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SYNTHESIS OF (2S, 3R, 4S), (2S, 3S, 4R)-EPOXYPROLINES AND AMINOHYDROXYPROLINES

J. Robinson, V. Lee, T. Claridge, J. Baldwin, C. Schofield
Published 1998 · Chemistry

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Abstract 2S, 3R, 4S- and 2S, 3S, 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.
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