Addition of carbonyl compounds to the cyclic olefins : synthesis of cyclitols

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2008

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Altun, Yasemin

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Cyclitols have attracted a great deal of attention in recent years owing to biological activities exhibited by them and also their usefulness in the synthesis of other natural products and pharmaceuticals. Carbasugars are also a derivative of cyclitols and they are cyclic monosaccharide analogues which posses CH2OH group in their structure. In this study, novel synthetic strategies leading to cyclitol derivatives were investigated and the synthesis of tetraol (72) and pentaol (73) derivatives containing CH2OH group were achieved successfully. Moreover, by the use of manganese(III) acetate oxidation reactions having considerable synthetic utilities in organic chemistry we developed new synthetic methodologies for the cyclitol derivatives. 1,3- and 1,4-Cyclohexadiene (71 and 10) were synthesized from easily available starting materials in order to be used as key compounds. The use of manganese(III) acetate oxidation reaction provides the creation of CH2OH group and one of the hydroxyl groups and the remaining hydroxyl groups were introduced into the key compounds by the use of singlet oxygen reaction. As a result of this, we had considerable advance in the synthesis of cyclitol derivatives.

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Chemistry.

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http://etd.lib.metu.edu.tr/upload/3/12610117/index.pdf
https://hdl.handle.net/11511/18063

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

Y. Altun, “Addition of carbonyl compounds to the cyclic olefins : synthesis of cyclitols,” M.S. - Master of Science, Middle East Technical University, 2008.