Cycloaddition Reactions of Deoxyribosylpropynoates
Pure anomers of either α or β 3-(2-deoxyribofuranosyl)propynoates reacted with the tetramethylcyclobutadiene–aluminum trichloride complex to yield the corresponding diastereoisomeric Dewar benzenes. Thermal- or ultraviolet light–initiated rearrangement gave rise
to highly substituted C-aryldeoxyribosides as single anomers. The same compounds as well as other substituted deoxyribosides were obtained also by transition metal–mediated cycloaddition reactions.
Keywords: C-aryldeoxyribosides; Dewar benzenes; cycloaddition; cyclotrimerization; unnatural nucleosides
Document Type: Research Article
Affiliations: 1: Charles University in Prague, Faculty of Science, Department of Organic Chemistry, Prague, Czech Republic 2: Charles University in Prague, Faculty of Science, Department of Inorganic Chemistry, Prague, Czech Republic 3: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic
Publication date: 03 May 2014
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