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.
ASJC Scopus subject areas
- Ceramics and Composites
- Electronic, Optical and Magnetic Materials
- Materials Chemistry
- Metals and Alloys
- Surfaces, Coatings and Films
Midtkandal, R. R., Macdonald, S. J. F., & Migaud, M. (2010). A stereocontrolled method for the synthesis of D- and L-2-deoxy-C-nucleosides using an intramolecular Sakurai-type cyclisation reaction. Chemical Communications, 46(25), 4538-4540. https://doi.org/10.1039/c0cc00467g