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J Org Chem

Title:		Synthesis of the Sex Pheromone of the Oleander Scale ( Aspidiotus nerii)
Author(s):		Castaneda MM; Bargues JM; Primo J; Fuertes IN;
Address:		"CEQA-Instituto Agroforestal del Mediterraneo , Universitat Politecnica de Valencia , Camino de Vera s/n, edificio 6C-5a planta, 46022 Valencia , Spain. Ecologia y Proteccion Agricola SL , Pol. Ind. Ciutat de Carlet , 46240 Carlet , Valencia , Spain"
Journal Title:		J Org Chem
Year:		2019
Volume:		20190618
Issue:		13
Page Number:		8578 - 8588
DOI:		10.1021/acs.joc.9b01001
ISSN/ISBN:		1520-6904 (Electronic) 0022-3263 (Linking)
Abstract:		"A total synthesis of the oleander scale [ Aspidiotus nerii (Bouche)] sex pheromone, the unique sesquiterpenoid containing a cyclobutane moiety of this class of compounds, has been developed. In order to implement this sex pheromone as a new environmentally friendly tool to manage this pest, a more cost-effective, multigram synthesis was required. This new synthetic route, having a Blaise reaction, iron-catalyzed carbon-carbon coupling, and [2 + 2] photocycloaddition reactions as key steps, provides a general access to 4-alkyl lactones as well as a robust access to the target sex pheromone. Starting from readily available compounds as 3-hydroxypropanenitrile, ethyl bromoacetate, and 2-acetyl butyrolactone, the synthetic sequence afforded the A. nerii sex pheromone with minimum intermediate purification and good overall yield in nine linear steps"
Keywords:		Animals Hemiptera/*physiology Molecular Structure Sex Attractants/*chemical synthesis;
Notes:		"MedlineCastaneda, Mary Montano Bargues, Javier Marzo Primo, Jaime Fuertes, Ismael Navarro eng Research Support, Non-U.S. Gov't 2019/06/28 J Org Chem. 2019 Jul 5; 84(13):8578-8588. doi: 10.1021/acs.joc.9b01001. Epub 2019 Jun 18"