Evaluation of the steric course of enoyl reduction in higher plants and insects via coupling to 1-alkene biosynthesis. A model study with Carthamus tinctorius(Asteraceae) and Tribolium castaneum(Coleoptera; Tenebrionidae)

Abstract

(E)-12-Phenyl[2-²H₂]dodec-2-enoic acid is in vivo reduced and oxidatively decarboxylated by plant (Carthamus tinctorius) and insect (Tribolium castaneum) model systems to (Z)-11-phenyl[1-²H]undec-1-ene; the known anti-elimination of the carboxy group and the C(3)-H_S hydrogen atom in conjunction with the (Z)-configuration of the alkene demands an anti-2Re,3Re addition of two hydrogen atoms across the double bond of the precursor acid.