Bioorganicheskaia khimiia 1987-08-01

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

Iu Iu Belosludtsev, G I Miagkova, R P Evstigneeva, N I Bobrova, K K Pivnitskiĭ

Index: Bioorg. Khim. 13(8) , 1125-31, (1987)

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Abstract

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.