A concise enantioselective entry to the synthesis of deoxy-azasugars

Org Lett. 2000 Jan;2(1):93-5. doi: 10.1021/ol991280u.

Abstract

[reaction: see text] A concise enantioselective preparation of oxazolidinylpiperidine 4, a key intermediate in the synthesis of glycosidase inhibitors such as 1-deoxymannojirimycin or 1-deoxygalactostatin, has been developed. Sharpless catalytic asymmetric epoxidation of (E)-2,4-pentadienol followed by treatment with allyl isocyanate afforded epoxy carbamate 8. Regioselective intramolecular ring opening promoted by sodium bis(trimethylsilyl)amide and ring-closing metathesis provided the bicyclic intermediate 4 in high enantiomeric purity. The four-step sequence takes place in 51% overall yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Deoxynojirimycin / chemical synthesis
  • Aza Compounds / chemical synthesis*
  • Aza Compounds / pharmacology
  • Deoxy Sugars / chemical synthesis*
  • Deoxy Sugars / pharmacology
  • Enzyme Inhibitors / chemical synthesis*
  • Galactosamine / analogs & derivatives
  • Galactosamine / chemical synthesis
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Molecular Structure
  • Piperidines / chemical synthesis
  • Piperidines / pharmacology
  • Stereoisomerism

Substances

  • Aza Compounds
  • Deoxy Sugars
  • Enzyme Inhibitors
  • Piperidines
  • 5-amino-5-deoxygalactopyranose
  • 1-Deoxynojirimycin
  • Galactosamine
  • Glycoside Hydrolases