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


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

CARBOHYDRATE RESEARCH, cilt.344, ss.426-431, 2009 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 344 Konu: 4
  • Basım Tarihi: 2009
  • Doi Numarası: 10.1016/j.carres.2008.12.005
  • Dergi Adı: CARBOHYDRATE RESEARCH
  • Sayfa Sayıları: ss.426-431

Özet

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.