Abstract
Pure anomers of either alpha or beta 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.