期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 1, 页码 88-95出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo801344f
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资金
- TUBITAK (Scientific and Technological Research Council of Turkey)
- Department of Chemistry at Middle East Technical University
- TUBA (Turkish Academy of Sciences)
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.
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