Self-sensitized photooxygenation of 3, 4-dialkoxyfurans to vitamin C or its derivatives

GH Hakimelahi, ML Jain, TW Ly, IC Chen…

Index: Hakimelahi; Jain; Tai Wei Ly; Chen; Ethiraj; Ru Hwu; Moshfegh Journal of Organic Chemistry, 2001 , vol. 66, # 21 p. 7067 - 7071

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Citation Number: 4

Abstract

Self-sensitized photooxygenation of 3, 4-dialkoxyfurans 3a-d with molecular oxygen and UV- or sunlight at room temperature gave vitamin C derivatives 2a-d in good to excellent yields. Furan 3c, having photodegradable protecting groups, was also photooxygenated to give l- ascorbic acid (1) in a “one-pot” reaction. Furthermore, a novel photolytic transformation was developed for deuteration of furan 3b at the C-2 position with D2O to give furan 3d in 95% ...

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