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J Org Chem

Title:		Synthesis of all 16 stereoisomers of pinesaw fly sex pheromones--tools and tactics for solving problems in fluorous mixture synthesis
Author(s):		Dandapani S; Jeske M; Curran DP;
Address:		"Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA"
Journal Title:		J Org Chem
Year:		2005
Volume:		70
Issue:		23
Page Number:		9447 - 9462
DOI:		10.1021/jo051526a
ISSN/ISBN:		0022-3263 (Print) 0022-3263 (Linking)
Abstract:		"[Reaction: see text]. The application of fluorous mixture synthesis (FMS) for accessing natural products and their stereoisomers was validated by the total synthesis of all 16 stereoisomers of the pine sawfly sex pheromone. Four fluorous p-methoxybenzyl groups were used as tags, and a '4-mix-4-split' approach was employed in a divergent synthesis. This paper presents the details of the FMS of pine sawfly sex pheromones with an emphasis on identification and solving of problems encountered when working with fluorous mixtures"
Keywords:		"Animals Chemistry, Organic/methods Female Fluorine/chemistry Hymenoptera/*chemistry Sex Attractants/*chemical synthesis/*chemistry Stereoisomerism;"
Notes:		"MedlineDandapani, Sivaraman Jeske, Mario Curran, Dennis P eng Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't 2005/11/05 J Org Chem. 2005 Nov 11; 70(23):9447-62. doi: 10.1021/jo051526a"