Tetrahedron

Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine.

AP Nin, O Varela, RM de Lederkremer

文献索引：Nin, Alejandro P.; Varela, Oscar; De Lederkremer, Rosa M. Tetrahedron, 1993 , vol. 49, # 42 p. 9459 - 9464

全文：HTML全文

被引用次数: 15

摘要

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 ...