Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors

Date

2009-01-02

Author

Baran, Arif
Balcı, Metin

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For the synthesis of various bishomo-inositol derivatives, 1,3,3a,7a-tetrahydro-2-benzofuran was used as the key compound. For further functionalization of the diene unit, the diene was subjected to photooxygenation, epoxidation, and cis-hydroxylation reactions. The endoperoxide linkage was cleaved by thiourea. The remaining double bond was subjected to epoxidation and cis-hydroxylation reactions. The epoxide rings and tetrahydrofuran rings formed were opened by acid-catalyzed reaction with sulfamic acid. The combination of these reactions resulted in the formation of various new inositol derivatives such as bishomo-chiro-inositol, bishomo-myo-inositol, and two isomeric bishomo-allo-inositols.

Subject Keywords

COST-EFFECTIVE CATALYST, STEREOSPECIFIC SYNTHESIS, FACIAL SELECTIVITY, SCYLLO-INOSITOL, SULFAMIC ACID, MUCO-INOSITOL, CONDURITOL-F, L-CHIRO, TRISPHOSPHATE, DERIVATIVES

URI

https://hdl.handle.net/11511/57683

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo801344f

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

A. Baran and M. Balcı, “Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors,” JOURNAL OF ORGANIC CHEMISTRY, pp. 88–95, 2009, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57683.