De novo enantioselective syntheses of galacto-sugars and deoxy sugars via the iterative dihydroxylation of dienoate.
An efficient route to various sugar lactones has been developed. Key to the overall transformation is the sequential osmium-catalyzed dihydroxylation of 2,4-dienoates. The simplest (one-step/racemic) example of this reaction occurs when the dihydroxylation is performed with aqueous NMO in MeOH. When the first dihydroxylation is performed using the AD-mix procedure, an enantioselective variant results. When a matched AD-mix procedure is used for the second dihydroxylation, an exceedingly diastereo- and enantioselective synthesis of galacto-1,4-lactone results. [Reaction: see text]
Ahmed
Md Moinuddin
MM
Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA.
Berry
Bryan P
BP
Hunter
Thomas J
TJ
Tomcik
Dennis J
DJ
O'Doherty
George A
GA
D003837:Deoxy Sugars / Q000138:chemical synthesis*; D005697:Galactosides / Q000138:chemical synthesis* / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D007783:Lactones / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D003837:Deoxy Sugars; D005697:Galactosides; D005960:Glucosides; D007783:Lactones