Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine.
AP Nin, O Varela, RM de Lederkremer
Index: Nin, Alejandro P.; Varela, Oscar; De Lederkremer, Rosa M. Tetrahedron, 1993 , vol. 49, # 42 p. 9459 - 9464
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Citation Number: 15
Abstract
An expeditious synthesis of cis-4-hydroxypipecolic acid (1) is described. The key step was diastereoselective hydrogenation of 2-acetamido-6-O-acetyl-2, 3, 5-trideoxy-hex-2-enono-1, 4-lactone (3), obtained in three high yielding steps from D-glucosamine. The formation of the piperidine ring from 2-amino-2, 3, 5-trideoxy-threo-hexono-1, 4-lactone derivative (10) was achieved by intramolecular nucleophilic displacement of the C-6 sulfonate by the C-2 ...
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