doi: 10.1021/ol051383e.
de novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation
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- PMID: 16119932
- DOI: 10.1021/ol051383e
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de novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation
Org Lett.
.
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. [reaction: see text]
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