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J Org Chem

Title:		Enantiospecific Synthesis of Both Enantiomers of the Longtailed Mealybug Pheromone and Their Evaluation in a New Zealand Vineyard
Author(s):		Ramesh R; Bell V; Twidle AM; Gonnade R; Reddy DS;
Address:
Journal Title:		J Org Chem
Year:		2015
Volume:		20150721
Issue:		15
Page Number:		7785 - 7789
DOI:		10.1021/acs.joc.5b01131
ISSN/ISBN:		1520-6904 (Electronic) 0022-3263 (Linking)
Abstract:		The irregular monoterpenoid sex pheromone of Pseudococcus longispinus and its enantiomer were prepared from the corresponding bornyl acetates. The use of readily accessible chiral starting materials and lactone-lactone rearrangement are the highlights of the present synthesis. The biological activities of the two enantiomers and racemic mixture were tested in a New Zealand vineyard. The (S)-(+)-enantiomer was significantly more attractive to P. longispinus males than the racemic mixture or the (R)-(-)-enantiomer
Keywords:		Animals Biological Phenomena Hemiptera/chemistry Lactones/*chemistry Male New Zealand Pheromones/*chemical synthesis Stereoisomerism;
Notes:		"MedlineRamesh, Remya Bell, Vaughn Twidle, Andrew M Gonnade, Rajesh Reddy, D Srinivasa eng Research Support, Non-U.S. Gov't 2015/07/15 J Org Chem. 2015 Aug 7; 80(15):7785-9. doi: 10.1021/acs.joc.5b01131. Epub 2015 Jul 21"