Pheromone Synthesis, CLXXXV Synthesis of the Analogues of Lurlenic Acid with a Modified Sugar Part: <i>Chlamydomonas</i> responds only to the <scp>D</scp>‐xyloside

Abstract

Abstract Six analogues of 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 )], the mating pheromone of Chlamydomonas allensworthii , were synthesized as E/Z mixtures ( E/Z = 3:2) at C‐12. They possess a tetrahydropyranyl ( 1a ), β‐ L ‐xylopyranosyl ( 1b ), β‐ D ‐glucopyranosyl ( 1e ) or β‐ D ‐arabinopyranosyl ( 1f ) group, respectively, as the sugar part. Only lurlenic acid ( 1 ) was bioactive as the pheromone.