Synthesis of bromo-conduritol-B and bromo-conduritol-C as glycosidase inhibitors.
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.
Cantekin
Seda
S
Department of Chemistry, Middle East Technical University, Ankara, Turkey.
Baran
Arif
A
Calişkan
Raşit
R
Balci
Metin
M
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
D004791:Enzyme Inhibitors; D007294:Inositol; D006026:Glycoside Hydrolases; D001966:Bromine