title: Synthesis of bromo-conduritol-B and bromo-conduritol-C as glycosidase inhibitors.
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 NaBH(4). Substitution of bromides bonded to sp(3)-hybridized carbon atoms with AgOAc gave the bromo-conduritol-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.
authors.affiliation: Department of Chemistry, Middle East Technical University, Ankara, Turkey.
authors.forename: Seda
authors.initials: S
authors.lastname: Cantekin
authors.forename: Arif
authors.initials: A
authors.lastname: Baran
authors.forename: Raşit
authors.initials: R
authors.lastname: Calişkan
authors.forename: Metin
authors.initials: M
authors.lastname: Balci
mesh_terms: D001966:Bromine / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D007294:Inositol / Q000031:analogs & derivatives* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D004791:Enzyme Inhibitors; D007294:Inositol; D006026:Glycoside Hydrolases; D001966:Bromine