Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton


BARAN A., Bekarlar M., Aydin G., NEBİOĞLU M., ŞAHİN E., BALCI M.

JOURNAL OF ORGANIC CHEMISTRY, vol.77, no.3, pp.1244-1250, 2012 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 77 Issue: 3
  • Publication Date: 2012
  • Doi Number: 10.1021/jo202494v
  • Title of Journal : JOURNAL OF ORGANIC CHEMISTRY
  • Page Numbers: pp.1244-1250

Abstract

1,3,3a,7a-Tetrahydro-2-benzofuran was used as key compound for the synthesis of various bishomoinositol derivatives. The diene was subjected to an epoxidation reaction for further functionalization of the diene unit. The bisepoxide obtained was submitted to a ring-opening reaction with acid in the presence of water. Various bishomoinositols were synthesized. However, when the reaction was carried out in the presence of acetic anhydride, a substituted 3-oxabicyclo[3.3.1]nonane skeleton was formed. The mechanism of the formation of the products is discussed.