Elsevier

Tetrahedron

Volume 54, Issues 5–6, 29 January 1998, Pages 981-996
Tetrahedron

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

https://doi.org/10.1016/S0040-4020(97)10352-0Get rights and content

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.

Preparations of epoxy and aminohydroxyprolines from trans-4-hydroxy-L-proline are described.

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