Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine.
1993; Elsevier BV; Volume: 49; Issue: 42 Linguagem: Inglês
10.1016/s0040-4020(01)80215-5
ISSN1464-5416
AutoresAlejandro P. Nin, Oscar Varela, Rosa M. de Lederkremer,
Tópico(s)Metabolism and Genetic Disorders
ResumoAn 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 amino group.
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