A stereocontrolled method for the synthesis of D- and L-2-deoxy-C-nucleosides using an intramolecular Sakurai-type
Rebecca R Midtkandal1, Simon J F Macdonald, Marie E Migaud
1Queen's University Belfast, School of Chemistry and Chemical Engineering, Belfast, BT9 5AG, UK.
Abstract:
A novel synthetic procedure has been developed that provides access to d/l-2-deoxy-C-nucleosides from 3,4-epoxytetrahydrofuran in seven steps and in moderate to good yields. The key chemical transformation was the Lewis acid catalysed intramolecular cyclisation reaction of an acetal for which the stereochemical outcome was dependent of the reagents' ratio.
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