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Synthesis of the Analogues of Lurlenic Acid with Modification in the Side-Chain or in the Aromatic Nucleus: Summary of the Structure−Activity Relationships

✍ Scribed by Shin-ichi Takanashi; Kenji Mori


Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
834 KB
Volume
1998
Category
Article
ISSN
1434-193X

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✦ Synopsis


Nine analogues of lurlenic acid {(4E,8E,12E)-14-[2Ј-hydroxy-nate (7), butyl lurlenate (8), the bisdemethyl analogue 9, and the 2Ј-deoxy-2Ј-methyl analogue 10. Structural requirements 3Ј,4Ј-dimethyl-5Ј-(1Љ-β-D-xylopyranosyloxy)phenyl]-4,8,12trimethyltetradeca-4,8,12-trienoic acid (1)}, a component of for the expression of the pheromonal activity is briefly discussed, indicating the importance of the sugar part, the phenolic the mating pheromone of the green flagellate Chlamydomonas allensworthii, were synthesized. They are the (12Z) iso-hydroxy group, the appropriate length and the unsaturation of the side-chain part, and the presence of a polar group at mer 2, the hexahydro derivative 3, the norprenyl analogue 4, the homoprenyl analogue 5, methyl lurlenate (6), ethyl lurle-the terminal position of the side-chain.


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