[Synthesis of the leukotriene A4 methyl ester via acetylene intermediates]

The strategy of acyclic eicosanoid synthesis via polyacetylenic intermediates is examplified by the synthesis of the racemic leukotriene A4 methyl ester. Leukotriene synthons, namely, trideca-1,4,7-triyne and methyl 6-formyl-5,6-trans-epoxyhexanoate, were synthesised using propargylic alcohol (thrice) and 1-heptyne as starting materials. In the course of the synthesis all new carbon-carbon bonds were created through acetylenide anion condensations and (Z)-double bonds are introduced by triple bond hydrogenations. The strategy provides a straightforward and stereospecific synthetic pathway.