Trisequential Photooxygenation Reaction: Application to the Synthesis of Carbasugars

BARAN A., Aydin G., Savran T., ŞAHİN E., BALCI M.

ORGANIC LETTERS, vol.15, no.17, pp.4350-4353, 2013 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 15 Issue: 17
  • Publication Date: 2013
  • Doi Number: 10.1021/ol401823m
  • Journal Name: ORGANIC LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4350-4353
  • Middle East Technical University Affiliated: No

Abstract

4,5-Dimethylenecyclohex-1-ene was subjected to a photooxygenation reaction to introduce oxygen functionalities. The endoperoxide obtained underwent an ene-reaction to form hydroperoxides with 1,3-diene structures. Further addition of singlet oxygen to the diene units resulted in the formation of tricyclic hydroperoxides having three oxygens in the molecule. Cleavage of the oxygen-oxygen bonds followed by epoxidation of the remaining C-C double bond and concomitant ring-opening reaction furnished the isomeric carbasugars.