Stereoselective Michael addition of carbon-, nitrogen-, oxygen-, and sulfur-centered nucleophiles on enantiopure hydroxylated 6,7-dehydro-5-oxoindolizidine. Synthesis of carbon- or hetero-7-substituted swainsonine analogues

J Org Chem. 2006 Aug 18;71(17):6630-3. doi: 10.1021/jo060511p.

Abstract

Enantiopure alpha,beta-unsaturated delta-lactams 1 and 2 react stereoselectively with carbon-, nitrogen-, sulfur-, and oxygen-centered nucleophiles. The synthetic potential of these conjugate additions is demonstrated through the synthesis of two new substituted indolizidines: (7R)-7-amino-8-deoxyswainsonine 3 and (7R)-7-acetylaminoswainsonine 4.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry*
  • Hydroxylation
  • Indolizines / chemistry*
  • Molecular Structure
  • Nitrogen / chemistry*
  • Oxygen / chemistry*
  • Stereoisomerism
  • Sulfur / chemistry*
  • Swainsonine / analogs & derivatives
  • Swainsonine / chemical synthesis
  • Swainsonine / chemistry*

Substances

  • 6,7-dehydro-5-oxoindolizidine
  • Indolizines
  • Sulfur
  • Carbon
  • Nitrogen
  • Swainsonine
  • Oxygen