Asymmetric synthesis of the four possible fagomine isomers

J Org Chem. 2003 May 2;68(9):3603-7. doi: 10.1021/jo034137u.

Abstract

The asymmetric synthesis of fagomine and its congeners 1-4 has been achieved by catalytic ring-closing metathesis (RCM). The synthesis involved the construction of the piperidene-type chiral building block 5 followed by dihydroxylation, starting from the d-serine-derived Garner aldehyde 6.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Combinatorial Chemistry Techniques*
  • Cyclization
  • Hydroxylation
  • Imino Pyranoses
  • Indicators and Reagents
  • Molecular Structure
  • Piperidines / chemical synthesis*
  • Stereoisomerism

Substances

  • Imino Pyranoses
  • Indicators and Reagents
  • Piperidines
  • fagomine