Total synthesis of deoxymannojirimycin and D-mannolactam via carbonylation of 5-vinyloxazolidin-2-ones

Academic Article

Abstract

  • The stereoselective synthesis of piperidine alkaloids deoxymannojirimycin and D-mannolactam from D-serine has been achieved. The key step involves palladium-catalysed decarboxylative carbonylation of a serine-derived 5-vinyloxazolidin-2-one to give 6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-1H-pyridin-2-one which was subsequently converted into the title compounds. © 2003 Elsevier Science Ltd. All rights reserved.
  • Authors

    Published In

  • Tetrahedron  Journal
  • Digital Object Identifier (doi)

    Author List

  • Knight JG; Tchabanenko K
  • Start Page

  • 281
  • End Page

  • 286
  • Volume

  • 59
  • Issue

  • 3