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

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

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Bibliographic Details
Published in:Tetrahedron 1998-01, Vol.54 (5), p.981-996
Main Authors: Kenneth Robinson, J., Lee, Victor, Claridge, Timothy D.W., Baldwin, Jack E., Schofield, Christopher J.
Format: Article
Language:English
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Summary:2 S, 3 R, 4 S- and 2 S, 3 S, 4 R-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. Preparations of epoxy and aminohydroxyprolines from trans-4-hydroxy- L-proline are described.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)10352-0