Pheromone Synthesis, CLXXIX. Synthesis of Lurlenic Acid and Lurlenol, the Sex Pheromones of the Green Flagellate <i>Chlamydomonas</i>

Abstract

Abstract Lurlenic acid {(4 E ,8 E ,12 E )‐14‐[2′‐hydroxy‐3′,4′‐dimethyl‐5′(1″‐β‐ D ‐xylopyranosyloxy)phenyl]‐4,8,12‐trimethyltetradeca‐4,8,12‐trienoic acid ( 1 )} and lurlenol ( 2 ), the sex pheromones produced by the female gametes of the green flagellate Chlamydomonas , were synthesized by starting from D ‐xylose, 2,3‐dimethyl‐ p ‐hydroquinone and geranylgeraniol or farnesol. Synthetic 1 and 2 were biologically active, while the possible biogenetic precursor 3 was inactive.