Abstract
A versatile and efficient route to both enantiomers of 4′-quaternary 2′-deoxy-3′- and -4′-epi-β-C- and -N-nucleosides is described. The asymmetric synthesis involves the SAMP/RAMP-hydrazone α-alkylation methodology and diastereoselective nucleophilic 1,2-additions. Manipulation of the substituents in the anomeric position leads to the thermodynamically more stable β-anomers of excellent diastereo- and enantiomeric purity (>99% de and ee).
Key words
nucleoside analogues - asymmetric synthesis - hydrazones - quaternary stereocentres - diastereoselective reduction
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