Syntheses of four D- and L-hexoses via diastereoselective and enantioselective dihydroxylation reactions.
An expeditious approach to various protected hexoses has been developed by the use of the Sharpless catalytic asymmetric dihydroxylation reaction. Applying the Sharpless catalytic asymmetric dihydroxylation reaction on vinylfuran, diols with high enantioexcess are produced. The resulting diols can be stereoselectively transformed into either protected D- or L-mannose in five steps and approximately 39% yield from furfural. Similarly, both D- and L-talose and gulose have been synthesized in 19% overall yields, respectively. Using a modified strategy, both protected D- and L-gulo- and allo-sugar-delta-lactones were synthesized in eight steps and approximately 20%, overall yield from furfural.
Harris
J M
JM
Department of Chemistry, University of Minnesota, Minneapolis 55455, USA.
Keränen
M D
MD
Nguyen
H
H
Young
V G
VG
O'Doherty
G A
GA
D005662:Furaldehyde / Q000737:chemistry; D006601:Hexoses / Q000138:chemical synthesis*; D006900:Hydroxylation; D007783:Lactones / Q000138:chemical synthesis; D008358:Mannose / Q000138:chemical synthesis; D013237:Stereoisomerism
D006601:Hexoses; D007783:Lactones; C057406:gulose; D005662:Furaldehyde; D008358:Mannose