De novo asymmetric syntheses of D- and L-talose via an iterative dihydroxylation of dienoates |
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Authors: | Ahmed Md Moinuddin O'Doherty George A |
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Affiliation: | Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA. |
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Abstract: | [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. |
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