Trisequential Photooxygenation Reaction: Application to the Synthesis of Carbasugars

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

ORGANIC LETTERS, cilt.15, sa.17, ss.4350-4353, 2013 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 15 Sayı: 17
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1021/ol401823m
  • Dergi Adı: ORGANIC LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.4350-4353
  • Orta Doğu Teknik Üniversitesi Adresli: Hayır

Özet

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.