STEREOSELECTIVE SYNTHESIS OF 3-HYDROXYMETHYL-D-CYCLOPENTENONE,THE VERSATILE INTERMEDIATE FOR THE SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES

The preparative and stereoselective synthesis (45–50% overall yields, >50 g scale) of the key carbasugars 7a–d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions.