Design, Synthesis, and Biological Activities of Some Branched Carbasugars: Construction of a Substituted 6-Oxabicyclo[3.2.1]nonane Skeleton

BARAN A., Cambul S., NEBİOĞLU M., BALCI M.

JOURNAL OF ORGANIC CHEMISTRY, cilt.77, sa.11, ss.5086-5097, 2012 (SCI-Expanded, Scopus) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 77 Sayı: 11
  • Basım Tarihi: 2012
  • Doi Numarası: 10.1021/jo300655p
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Sayfa Sayıları: ss.5086-5097
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

Transformation of c-yclohexa-2,4-diene-1,2-diylbis(methylene) diacetate to various carbasugars is described. Photooxygenation of a cyclohexadiene derivative gave a bicyclic endoperoxide, which was reduced with thiourea to [2-Racetyloxy)methyl]cyclohexa-2,4-dien-l-yl]methyl acetate. Epoxidation of the remaining double bond followed by epoxide ring-opening and hydrolysis of the acetate groups gave one of the target hexols. The bicyclic endoperoxide was rearranged to a diepoxide with CoTPP. The diepoxide was reacted with sulfamic acid in acetic anhydride, resulting in the formation of a new branched carbasugar as well as in the formation of cyclitols with a 6-oxabicyclo[3.2.1]nonane skeleton. The mechanism of the formation of the products is discussed. The inhibition activity of six cyclitol derivatives was tested against a-glycosidase.