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J Org Chem

Title:		"An asymmetric synthesis of (+)-grandisol, a constituent of the aggregation pheromone of the cotton boll weevil, via a kinetic resolution"
Author(s):		Hamon DP; Tuck KL;
Address:		"The Department of Chemistry, The University of Adelaide, S.A. 5005, Australia"
Journal Title:		J Org Chem
Year:		2000
Volume:		65
Issue:		23
Page Number:		7839 - 7846
DOI:		10.1021/jo000853+
ISSN/ISBN:		0022-3263 (Print) 0022-3263 (Linking)
Abstract:		"A novel approach to the asymmetric synthesis of (+)-grandisol, (1R, 2S)-isopropenyl-1-methylcyclobutaneethanol, involves the use of catalytic kinetic resolution of a primary allylic alcohol, [(1RS, 5SR)-5-methylbicyclo[3.2.0]hept-2-en-2-yl] methanol. The allylic alcohol is prepared in four steps from simple achiral materials involving the use of a modified Shapiro reaction. The resolved alcohol (95% ee) is then reduced in two steps to the corresponding methyl alkene, (1S,5R)-2,5-dimethylbicyclo[3.2.0]hept-2-ene. This alkene is converted to (+)-grandisol (95% ee), in three steps, by modified literature procedures"
Keywords:		Pheromones/*chemical synthesis Stereoisomerism Terpenes/*chemical synthesis;
Notes:		"MedlineHamon, D P Tuck, K L eng Research Support, Non-U.S. Gov't 2000/11/14 J Org Chem. 2000 Nov 17; 65(23):7839-46. doi: 10.1021/jo000853+"