Tetrahedron Letters

Synthesis of deuterated 5 (Z), 11 (Z)-eicosadienoic acid as a biomarker for trophic transfer

S Albu, E Sverko, MT Arts, A Capretta

Index: Albu, Siliva; Sverko, Ed; Arts, Michael T.; Capretta, Alfredo Tetrahedron Letters, 2011 , vol. 52, # 7 p. 787 - 788

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Citation Number: 6

Abstract

Despite having been isolated from a variety of natural sources, the synthesis of 5(Z),11(Z)-eicosadienoic acid (1) has not been described in the literature. The synthetic route developed appears in Scheme 1 and Scheme 2. The approach was designed so as to insure cis stereochemistry at C5 C6 and C11 C12 by taking advantage of an alkyne reduction using Lindlar's catalyst. Furthermore, the route offers the opportunity to introduce deuterium at either alkene or both as desired.