A new route, of potential strategic importance, to a difluorosugar analogue has been developed. Key steps included a Stille coupling and a highly regio- and enantioselective dihydroxylation of a highly substituted diene. Protecting groups were chosen to enhance the reactivity of the disubstituted allylic fragment in the AD reaction and allow deprotection under orthogonal conditions.
- catalytic sysnthesis
- Stille coupling
- orthogonal conditions
Cox, L. R., DeBoos, G. A., Fullbrook, J. J., Percy, J., Spencer, N. S., & Tolley, M. (2003). Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose. Organic Letters, 5(3), 337-339 . https://doi.org/10.1021/ol02735