A new and stereospecific synthesis of an inositol analogue: bis-homoinositol


Kara Y., Balci M.

TETRAHEDRON, vol.59, no.12, pp.2063-2066, 2003 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 59 Issue: 12
  • Publication Date: 2003
  • Doi Number: 10.1016/s0040-4020(03)00209-6
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.2063-2066
  • Keywords: cyclitols, peroxides, bicyclic aliphatic compounds, oxidation, CHIRO-INOSITOL, MYOINOSITOL, DERIVATIVES, CONDURITOLS

Abstract

The photooxygenation of trans-8-(acetyloxy)bicyclo[4.2.0]octa-2,4-dien-7-yl acetate afforded the bicyclic endoperoxide. Reduction of the endoperoxide with thiourea followed by acetylation gave the corresponding tetraacetate. The KMnO4 oxidation of the tetraacetate followed by acetylation gave dihydroxytetraacetate Ammonolysis of tetraacetate afforded the bis-homoinositol, bicyclo[4.2.0]octane-2,3,4,5,7,8-hexol. (C) 2003 Elsevier Science Ltd. All rights reserved.