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J Org Chem

Title:		Intramolecular carbolithiation as a route to a sterically congested cyclopentene: synthesis of the longtailed mealybug pheromone
Author(s):		Bailey WF; Bakonyi JM;
Address:		"Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, USA. william.bailey@uconn.edu"
Journal Title:		J Org Chem
Year:		2013
Volume:		20130313
Issue:		7
Page Number:		3493 - 3495
DOI:		10.1021/jo4002118
ISSN/ISBN:		1520-6904 (Electronic) 0022-3263 (Linking)
Abstract:		"A concise preparation of the pheromone secreted by the female longtailed mealybug [viz., 2-(1,5,5-trimethylcyclopent-2-en-1-yl)ethyl acetate] (1) is described. The key step in the synthesis of 1 involves 5-exo-trig ring closure of the vinyllithium derived from (Z)-1-iodo-4,4,5-trimethyl-1,5-hexadiene by lithium-iodine exchange"
Keywords:		Acetates/*chemical synthesis/chemistry Cyclopentanes/chemical synthesis/*chemistry Lithium/*chemistry Molecular Structure Organometallic Compounds/chemical synthesis/*chemistry;
Notes:		"MedlineBailey, William F Bakonyi, Johanna M eng Research Support, Non-U.S. Gov't 2013/03/09 J Org Chem. 2013 Apr 5; 78(7):3493-5. doi: 10.1021/jo4002118. Epub 2013 Mar 13"