synthesis of (2r,5r)-2-amino-5-hydroxyhexanoic acid by intramolecular cycloaddition

synthesis of (2r,5r)-2-amino-5-hydroxyhexanoic acid by intramolecular cycloaddition

;Elliad R. Silcoff;Tuvia Sheradsky
Journal of ethnopharmacology 1998 Vol. 3 pp. 80-87
193
silcoff1998moleculessynthesis

Abstract

The title compound was synthesized from sorbic acid by an eight step sequence. The key step was the stereospecific intramolecular Diels-Alder reaction of the acylnitroso derivative of N-sorbyl-L-proline (5). L-Proline served as a temporary tether which directed both the stereochemistry and the regiochemistry of the cycloaddition.

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