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Pheromone Synthesis, CLXXIX . Synthesis of Lurlenic Acid and Lurlenol, the Sex Pheromones of the Green Flagellate Chlamydomonas
Author(s) -
Takanashi ShinIchi,
Mori Kenji
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970507
Subject(s) - sex pheromone , flagellate , chemistry , farnesol , geranylgeraniol , stereochemistry , chlamydomonas , pheromone , biochemistry , botany , biology , gene , mutant
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.