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, vol.77, no.11, pp.5086-5097, 2012 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 77 Issue: 11
  • Publication Date: 2012
  • Doi Number: 10.1021/jo300655p
  • Journal Name: JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.5086-5097
  • Middle East Technical University Affiliated: Yes

Abstract

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.