Synthesis of bromo-conduritol-B and bromo-conduritol-C as glycosidase inhibitors


Cantekin S., Baran A., Caliskan R., BALCI M.

CARBOHYDRATE RESEARCH, vol.344, no.4, pp.426-431, 2009 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 344 Issue: 4
  • Publication Date: 2009
  • Doi Number: 10.1016/j.carres.2008.12.005
  • Title of Journal : CARBOHYDRATE RESEARCH
  • Page Numbers: pp.426-431
  • Keywords: Quinones, Endoperoxides, Conduritol-B, Conduritol-C, Haloconduritol, Enzyme inhibition, HIGH-TEMPERATURE BROMINATION, CHEMOENZYMATIC SYNTHESIS, MONOSUBSTITUTED BENZENES, STEREOSPECIFIC SYNTHESIS, OXIDATION, DIOXIDES, HYDROQUINONES, DERIVATIVES, MECHANISM

Abstract

For the synthesis of bromo-conduritol-B skeleton, bromo-1,4-benzoquinone was subjected to bromination followed by the reduction of the carbonyl groups with NaBH4. Substitution of bromides bonded to sp(3)-hybridized carbon atoms with AgOAc gave the bromo-concluritol-B tetraacetate in high yield. For the construction of bromo-conduritol-C skeleton, 2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole was used as the starting material. Photooxygenation of the diene unit gave an unsaturated bicyclic endoperoxide. Bromine was incorporated into the molecule by the addition of bromine to the double bond. Opening of the peroxide linkage followed by HBr elimination and reduction of the carbonyl group provided the conduritol-C structure in good yield. Bromo-conduritol-B exhibited strong enzyme-specific inhibition against alpha-glycosidase. (C) 2008 Elsevier Ltd. All rights reserved.