A stereocontrolled method for the synthesis of D- and L-2-deoxy-C-nucleosides using an intramolecular Sakurai-type cyclisation reaction.
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.
Midtkandal
Rebecca R
RR
Queen's University Belfast, School of Chemistry and Chemical Engineering, Belfast, BT9 5AG, UK.
Macdonald
Simon J F
SJ
Migaud
Marie E
ME
D003500:Cyclization; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009705:Nucleosides