Synthesis of branched carbasugars via photooxygenation and manganese(III) acetate free radical cyclization |
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| Authors: | Yasemin Altun Sengul Dilem Dogan Metin Balci |
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| Institution: | 1. Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey;2. Department of Pharmaceutical Basic Sciences, Faculty of Pharmacy, Erciyes University, 38039 Kayseri, Turkey |
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| Abstract: | Transformation of cyclohexa-1,3- and 1,4-dienes to carbasugars is described. Photooxygenation of dienes gave bicyclic endoperoxides, which were reduced with thiourea to the corresponding 1,4-diols with cis-configuration. Lactonization of the remaining double bond by oxidative addition of acetic acid to the double bond in the presence of Mn(OAc)3 followed by lactone ring-opening reaction gave the target branched carbasugars. |
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| Keywords: | Cyclitol Carbasugars Branched carbasugars Photooxygenation Mn(OAc)3 oxidation |
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