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J Org Chem

Title:		"Bidirectional Synthesis of 6-Acetoxy-5-hexadecanolide, the Mosquito Oviposition Pheromone of Culex quinquefasciatus, from a C(2)-Symmetric Building Block Using Olefin Metathesis Reactions"
Author(s):		Schmidt B; Petersen MH; Braun D;
Address:		"Universitaet Potsdam , Institut fuer Chemie, Karl-Liebknecht-Strasse 24-25, D-14476 Potsdam-Golm, Germany"
Journal Title:		J Org Chem
Year:		2018
Volume:		20180112
Issue:		3
Page Number:		1627 - 1633
DOI:		10.1021/acs.joc.7b02944
ISSN/ISBN:		1520-6904 (Electronic) 0022-3263 (Linking)
Abstract:		"(5R,6S)-6-Acetoxy-5-hexadecanolide (MOP) is the oviposition pheromone of the mosquito Cx. quinquefasciatus, a vector of pathogens causing a variety of tropical diseases. We describe and evaluate herein three syntheses of MOP starting from mannitol-derived (3R,4R)-hexa-1,5-diene-3,4-diol. This C(2)-symmetric building block is elaborated through bidirectional olefin metathesis reactions into 6-epi-MOP, which was converted into MOP via Mitsunobu inversion. The shortest of the three routes makes use of two sequential cross-metathesis reactions and an assisted tandem catalytic olefin reduction, induced by an in situ conversion of a Ru-carbene to a Ru-hydride"
Keywords:		Alkenes/*chemistry Animals Culex Molecular Conformation *Oviposition Pheromones/*chemistry Pyrones/*chemical synthesis/chemistry;
Notes:		"MedlineSchmidt, Bernd Petersen, Monib H Braun, Diana eng Research Support, Non-U.S. Gov't 2018/01/03 J Org Chem. 2018 Feb 2; 83(3):1627-1633. doi: 10.1021/acs.joc.7b02944. Epub 2018 Jan 12"