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Org Lett

Title:		"Highly alpha-selective hydrolysis of alpha,beta-epoxyalcohols using tetrabutylammonium fluoride"
Author(s):		Mukerjee P; Abid M; Schroeder FC;
Address:		"Boyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, USA"
Journal Title:		Org Lett
Year:		2010
Volume:		12
Issue:		18
Page Number:		3986 - 3989
DOI:		10.1021/ol1015306
ISSN/ISBN:		1523-7052 (Electronic) 1523-7060 (Print) 1523-7052 (Linking)
Abstract:		"We report a simple method for the highly regio- and stereoselective hydrolysis of alpha,beta-epoxyalcohols. Treatment of enantiopure epoxyalcohols derived from Sharpless epoxidation with TBAF/H(2)O resulted in exclusive ring opening at the normally disfavored alpha-position, providing access to arabino- or lyxo-configured triols with full preservation of stereochemical purity. The method was applied in syntheses of 5-deoxy-l-arabinose (26) and a family of bicyclic acetals based on the insect pheromone hydroxybrevicomin (4)"
Keywords:		Alcohols/*chemistry Biological Products/chemistry Epoxy Compounds/*chemistry Hydrolysis Molecular Structure Quaternary Ammonium Compounds/*chemistry;
Notes:		"MedlineMukerjee, Purba Abid, Mohammed Schroeder, Frank C eng P41 GM079571/GM/NIGMS NIH HHS/ P41 GM079571-02/GM/NIGMS NIH HHS/ P41 GM079571-03S1/GM/NIGMS NIH HHS/ GM079571/GM/NIGMS NIH HHS/ Research Support, N.I.H., Extramural 2010/08/21 Org Lett. 2010 Sep 17; 12(18):3986-9. doi: 10.1021/ol1015306"