Syntheses of long-chain acids. Part VIII. 9,10,18-Trihydroxyoctadecanoic acids

Abstract

Condensation of the dilithio-derivative of dec-9-yn-1-ol with 8-bromo-octanoic acid gives 18-hydroxyoctadec-9-ynoic acid which is converted, by semihydrogenation and hydroxylation, into threo- and erythro-9,10,18-trihydroxyoctadecanoic acids (phloionolic and isophloionolic acids). Similar condensations give 22-hydroxydocos-12-ynoic and 24-hydroxytetracos-14-ynoic acids and thence the saturated ω-hydroxy-acids.