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Synthesis of branched carbasugars via photooxygenation and manganese(III) acetate free radical cyclization

2014-08-19
Altun, Yasemin
Dogan, Sengul Dilem
Balcı, Metin
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-dials 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.