Pheromone Synthesis, CLXXXV Synthesis of the Analogues of Lurlenic Acid with a Modified Sugar Part:Chlamydomonas responds only to theD-xyloside

✍ Scribed by Takanashi, Shin-Ichi ;Mori, Kenji

• Book ID: 102365985
• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 484 KB
• Volume: 1997
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199719970606

✦ Synopsis

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.