De Novo Asymmetric Synthesis of Daumone via a Palladium-Catalyzed Glycosylation
Organic Letters2005Vol. 7(18), pp. 3921–3924
Citations Over TimeTop 10% of 2005 papers
Abstract
The enantioselective syntheses of daumone and two analogues have been achieved in seven to eight steps. This route relies upon a diasteroselective palladium-catalyzed glycosylation reaction for the formation of the anomeric bond. The asymmetry of the sugar and aglycone portion of daumone were introduced by Noyori reduction of an acylfuran and a propargyl ketone. A highly diastereoselective epoxidation and reductive ring opening established the desired C-2 and C-4 stereochemistry of daumone.
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