Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose.
[reaction: see text] 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.
Cox
Liam R
LR
School of Chemical Sciences, University of Birmingham, Edgbaston, Birmingham B15 2TT, United Kingdom.
DeBoos
Gareth A
GA
Fullbrook
Jeremy J
JJ
Percy
Jonathan M
JM
Spencer
Neil S
NS
Tolley
Malcolm
M
D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D014996:Xylulose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
C473426:1-deoxy-1,1-difluoro-D-xylulose; D014996:Xylulose