Add time:08/14/2019         Source:sciencedirect.com

(3Z,6Z,9Z,12E)-Pentadecatetraenal, a common intermediate in the synthesis of methyl Δl7t EPA and methyl Δl9t DHA, was obtained by copper(I)-catalyzed coupling between the Grignard reagent of 1,1-diethoxy-3-butyne and (Z,E)-l-bromo-5,8-undecadien-2-yne followed by semi-hydrogenation of the resulting diendyne. The tetraenic aldehyde was subjected to a Wittig reaction with the ylide of (3-carboxybutyl)triphenylphosphonium bromide or of [6-(2,6,7-trioxabicyclo [2.2.2] octyl)-hex-3-Z-enyl] triphenylphosphonium iodide to give, respectively Δl7t EPA and the protected Δl9t DHA in high isomeric purity.

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