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Org Lett. 2005 Sep 1;7(18):3921-4.

de novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation.

Author information

1
Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA.

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].

PMID:
16119932
DOI:
10.1021/ol051383e
[Indexed for MEDLINE]

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