Development of new synthetic strategies for aminocyclitols

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2003
Demir (Davulcu), Emine
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Cyclitols are of great importance due to their biological activities playing a crucial role in living organisms as well as their synthetic usefulness in the synthesis of other natural compounds or pharmaceuticals. In this study, new synthetic strategies leading to the aminocyclitols were investigated. The synthesis of aminoconduritol and aminoinositol derivatives (173 and 174) were achieved starting from easily available compound, 7-oxa-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (166) obtained from the Diels-Alder reaction of furan and maleic anhydride. The anhydride functionality in 166 was converted into the half-ester 169 by desymmetrization in methanol. The carboxylic acid moiety in the molecule was used to obtain urethane functionality by making use of Curtius rearrangement. After the cleavage of oxa-bridge with the help of a Lewis acid the aminoconduritol derivative 173 was synthesized. The cis-dihydroxylation of 173 with osmium tetroxide resulted in the formation of inositol derivative 174. Consequently, we developed a new methodology for the synthesis of aminocyclitol derivatives.
Amino acids, Aminocyclitols, Aminoconduritols, Aminoinositols, Desymmetrization of anhydride, Curtius rearrangement, Ring opening of oxa-bridge
http://etd.lib.metu.edu.tr/upload/1045525/index.pdf
https://hdl.handle.net/11511/13629
Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats
E. Demir (Davulcu), “Development of new synthetic strategies for aminocyclitols,” M.S. - Master of Science, Middle East Technical University, 2003.
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