Tetrahedron

Synthesis of (S)-(+)-enantiomers of food-relevant (n-5)-monoenoic and saturated anteiso-fatty acids by a Wittig reaction

S Thurnhofer, W Vetter

Index: Thurnhofer, Saskia; Vetter, Walter Tetrahedron, 2007 , vol. 63, # 5 p. 1140 - 1145

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Citation Number: 15

Abstract

We developed an enantioselective synthesis for the food-relevant anteiso-fatty acids a15: 0, a16: 0, and a17: 0. Different (carboxyalkyl) triphenylphosphonium bromide salts were coupled with (S)-3-methylpentanal in a Wittig reaction. Mixtures of the obtained cis-/trans- isomers were separated by Ag+-HPLC to give the novel cis-isomers of (S)-(+)-a15: 1n-5,(S)- (+)-a16: 1n-5, and (S)-(+)-a17: 1n-5. Hydrogenation of the monoenoic products led to (S)-( ...