De novo asymmetric syntheses of D- and L-talose via an iterative dihydroxylation of dienoates.
[reaction: see text] A short and highly efficient route to D- and L-talo-gamma-lactones has been developed. The key transformation was the sequential osmium-catalyzed bis-dihydroxylation reaction of substituted 2,4-dienoates. When the first dihydroxylation reaction is performed on (2Z,4E)-dienoates with use of the Sharpless AD-mix procedure, a regio- and enantioselective dihydroxylation resulted along with an in situ lactonization. A subsequent dihydroxylation, using OsO4/NMO in MeOH conditions, resulted in an exceedingly diastereo- and enantioselective synthesis of talo-gamma-lactone.
Ahmed
Md Moinuddin
MM
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
O'Doherty
George A
GA
D002087:Butyrates / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis; D006900:Hydroxylation; D007783:Lactones / Q000138:chemical synthesis*; D009574:Nitro Compounds / Q000737:chemistry; D013237:Stereoisomerism
C508635:6-(nitrooxy)hexyl-(2z)-4-(acetyloxy)-3-(4-(methylsulfonyl)phenyl)-2-phenylbut-2-enoate; D002087:Butyrates; D002241:Carbohydrates; C510913:L-talo-gamma-lactone; D007783:Lactones; D009574:Nitro Compounds