De novo asymmetric syntheses of C-4-substituted sugars via an iterative dihydroxylation strategy.
A short and highly efficient route to various C-4 substituted sugar lactones has been developed. The key to the overall transformation is the sequential osmium-catalyzed dihydroxylation reaction of substituted 2,4-dienoates and an allylic substitution at the C-4 position. When the Sharpless AD-mix procedure is used in a matched sense for the second dihydroxylation reaction, it results in an exceedingly diastereo- and enantioselective synthesis of several C-4-substituted sugars.
Ahmed
Md Moinuddin
MM
Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA.
O'Doherty
George A
GA
D005942:Gluconates / Q000138:chemical synthesis; D006900:Hydroxylation; D007783:Lactones / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013400:Sugar Acids / Q000138:chemical synthesis
D005942:Gluconates; D007783:Lactones; D013400:Sugar Acids; C007813:galactonolactone; C014962:altronic acid; C010730:beta-glucono-1,5-lactone