Stereoselective Synthesis of (5R, 65)-(-) Erythro-6-Acetoxy-5-Dodecanolide,A Lower Homologue of a Mosquito Oviposition Attractant Pheromone,from Argentilactone |
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| Authors: | Luis F Sala Raquel M Cravero Sandra R Signorella Manuel González-Sierra Edmundo A Rúveda |
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| Institution: | Institute de Quimica Organica de Sintesis (CONICET-UNR), Facultad de Ciencias Bioquimicas y Farmaceuticas , Casilla de Correo 991, 2000, Rosario, Argentina |
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| Abstract: | Starting from argentilactone (5R)-(-)- δ -lactone of 5-hydroxydodeca-Z,Z-2,6-dienoic acid] and via the hydrobromic acid opening of the 65, 75-epoxide followed by acetylation and catalytic hydrogenation of the corresponding bromohydrin, (5R, 65)-(-)-erythro-6-acetoxy-5-dodecanolide was obtained. Through the 6R, 7R-epoxide and following the same sequence, the stereoisomer (5R, 6R)-(+)-threo-6-acetoxy-5-dodecanolide, was also synthesized. |
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