Intramolecular aldol cyclization of L-lyxo-hexos-5-ulose derivatives: a new diastereoselective synthesis of D-chiro-inositol

Bioorg Med Chem Lett. 2002 Nov 18;12(22):3313-5. doi: 10.1016/s0960-894x(02)00692-3.

Abstract

The DBU-promoted intramolecular aldol condensation of two partially protected L-lyxo-hexos-5-ulose derivatives (8 and 9), in turn obtained starting from methyl beta-D-galactopyranoside, takes place with fairly good yield and complete diastereoselectivity to give 2L-(2,3,6/4,5)-pentahydroxycyclohexanone derivatives, 10 and 11. The stereoselective reduction of inosose 10 with sodium triacetoxyborohydride leads, after catalytic debenzylation, to D-chiro-inositol (1), while the sodium borohydride reduction furnishes, with opposite stereoselectivity, a derivative of allo-inositol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Inositol / analogs & derivatives*
  • Inositol / chemical synthesis*
  • Inositol / chemistry
  • Mannose / analogs & derivatives*
  • Mannose / chemistry
  • Methylgalactosides / chemistry
  • Stereoisomerism

Substances

  • 5-ketomannose
  • Methylgalactosides
  • inosose
  • Inositol
  • Mannose