Total Synthesis and Biological Activity of 13,14‐Dehydro‐12‐Oxo‐Phytodienoic Acids (Deoxy‐J₁‐Phytoprostanes)

Abstract

Archetype lipid signals in plants. Non-enzymatic oxidation of linolenate yields a series of prostaglandin-like stress metabolites including racemic deoxy-J1-phytoprostanes (1) that are structurally related to 12-oxo-phytodienoic acid (2). Naturally occurring isomers of 1 were prepared by total synthesis and tested in three bioassay systems to reveal potent jasmonate-like activities.