S. Takanashi, K. Mori
1998
Citations
0
Influential Citations
5
Citations
Journal
European Journal of Organic Chemistry
Abstract
Nine analogues of lurlenic acid {(4E,8E,12E)-14-[2′-hydroxy-3′,4′-dimethyl-5′-(1′′-β-D-xylopyranosyloxy)phenyl]-4,8,12-trimethyltetradeca-4,8,12-trienoic acid (1)}, a component of the mating pheromone of the green flagellate Chlamydomonasallensworthii, were synthesized. They are the (12Z) isomer 2, the hexahydro derivative 3, the norprenyl analogue 4, the homoprenyl analogue 5, methyl lurlenate (6), ethyl lurlenate (7), butyl lurlenate (8), the bisdemethyl analogue 9, and the 2′-deoxy-2′-methyl analogue 10. Structural requirements for the expression of the pheromonal activity is briefly discussed, indicating the importance of the sugar part, the phenolic hydroxy group, the appropriate length and the unsaturation of the side-chain part, and the presence of a polar group at the terminal position of the side-chain.