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Org Lett

Title:		de novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation
Author(s):		Guo H; O'Doherty G;
Address:		"Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA"
Journal Title:		Org Lett
Year:		2005
Volume:		7
Issue:		18
Page Number:		3921 - 3924
DOI:		10.1021/ol051383e
ISSN/ISBN:		1523-7060 (Print) 1523-7052 (Linking)
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]
Keywords:		Animals Caenorhabditis elegans/chemistry Catalysis Fatty Acids/*chemical synthesis Glycosylation Molecular Structure Palladium/*chemistry Pheromones/*chemical synthesis Stereoisomerism;
Notes:		"MedlineGuo, Haibing O'doherty, George A eng Research Support, N.I.H., Extramural Research Support, U.S. Gov't, Non-P.H.S. Research Support, U.S. Gov't, P.H.S. 2005/08/27 Org Lett. 2005 Sep 1; 7(18):3921-4. doi: 10.1021/ol051383e"