Preparation of carbocyclic analogues of 2′-deoxyribonucleotides possessing a phosphonate substituent at the 5′-position
Abstract
The epoxycyclopentanol 10 is converted into the methylphosphonate 15 in 30% overall yield. The diol 15 is converted into the protected carbocyclic nucleotide mimics 16, 18, 21 and 22 in 38–70% yield. The diol 15 is resolved using a lipase-catalysed esterification and the absolute configurations of the enantiomers are deduced by CD spectroscopy.