Stereoselective synthesis of bishomo-inositols as glycosidase inhibitors

J Org Chem. 2009 Jan 2;74(1):88-95. doi: 10.1021/jo801344f.

Abstract

For the synthesis of various bishomo-inositol derivatives, 1,3,3a,7a-tetrahydro-2-benzofuran was used as the key compound. For further functionalization of the diene unit, the diene was subjected to photooxygenation, epoxidation, and cis-hydroxylation reactions. The endoperoxide linkage was cleaved by thiourea. The remaining double bond was subjected to epoxidation and cis-hydroxylation reactions. The epoxide rings and tetrahydrofuran rings formed were opened by acid-catalyzed reaction with sulfamic acid. The combination of these reactions resulted in the formation of various new inositol derivatives such as bishomo-chiro-inositol, bishomo-myo-inositol, and two isomeric bishomo-allo-inositols.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Inositol / analogs & derivatives*
  • Inositol / chemical synthesis*
  • Inositol / chemistry
  • Inositol / pharmacology
  • Kinetics
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Enzyme Inhibitors
  • Inositol
  • Glycoside Hydrolases