Synthesis of bicyclo[2.2.2]octane-2,3,5,6,7,8 hexols (Bishomoinositols) as glycosidase inhibitors

Date

2008-06-20

Author

Baran, Arif
Guenel, Aslihan
Balcı, Metin

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For the construction of the bicyclo[2.2.2] octane skeleton, 2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole was reacted with vinylene carbonate to give two isomeric cycloadditon products having the bicyclo[2.2.2]octane skeleton. Hydrolysis of the ketal ring and the opening of the carbonate functionality, followed by hydroxylation of the remaining double bond resulted in the formation of a symmetrical hexol. Epoxidation of the double bond in the cycloaddition products and the subsequent ring-opening reactions produce two additional hexol derivatives. One of the synthesized molecules exhibited enzyme-specific inhibition against alpha-glycosidase.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/57615

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo800553u

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Graduate School of Natural and Applied Sciences, Article

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Citation Formats

A. Baran, A. Guenel, and M. Balcı, “Synthesis of bicyclo[2.2.2]octane-2,3,5,6,7,8 hexols (Bishomoinositols) as glycosidase inhibitors,” JOURNAL OF ORGANIC CHEMISTRY, pp. 4370–4375, 2008, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57615.