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

Date

2009-03-10

Author

Cantekin, Seda
Baran, Arif
Caliskan, Rasit
Balcı, Metin

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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.

Subject Keywords

Quinones, Endoperoxides, Conduritol-B, Conduritol-C, Haloconduritol, Enzyme inhibition

URI

https://hdl.handle.net/11511/51685

Collections

Graduate School of Natural and Applied Sciences, Article