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

Kara Y., Balci M.

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

  • Publication Type: Article / Article
  • Volume: 59 Issue: 12
  • Publication Date: 2003
  • Doi Number: 10.1016/s0040-4020(03)00209-6
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2063-2066
  • Keywords: cyclitols, peroxides, bicyclic aliphatic compounds, oxidation, CHIRO-INOSITOL, MYOINOSITOL, DERIVATIVES, CONDURITOLS
  • Middle East Technical University Affiliated: No

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.