Diastereoselective synthesis of (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives

Org Lett. 2004 Dec 23;6(26):4941-4. doi: 10.1021/ol047774v.

Abstract

[reaction: see text] Herein, we report a diastereoselective synthesis of the natural product (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives thereof. The key step in the synthetic sequence is a novel highly diastereoselective epoxidation reaction of an enantiomerically pure cyclic enamide intermediate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Conformation
  • Pipecolic Acids / chemical synthesis*
  • Pipecolic Acids / chemistry
  • Stereoisomerism

Substances

  • Pipecolic Acids
  • 5-hydroxypipecolic acid