Lurlenic acid

Lurlenic acid (23) is the sex pheromone produced by the female gametes of the green flagellate Chlamydomonas allensworthii to attract the male gametes. Mori s synthesis of 23 is summarized in Scheme 36 [59]. The aglycone part C was prepared by coupling A with B. 

In 1995 Starr el al. in the USA reported the chemoattraction of male gametes by female gametes of a new species of the green flagellate, Chlamydomonas allensworthii. The female-produced attractant pheromone was isolated and identified as 168 by Jaenicke and Marner in Germany. They coined the name lurlenic acid to 168, because they worked in Cologne near the Rock of Lorelei. The pheromone 168 attracts the male gametes at a concentration as low as 10-12M. 

Mainly because of its unique structure and bioactivity and partly because of my personal interest in Chlamydomonas chemistry, we undertook the synthesis of lurlenic acid (168) basing on the retrosynthetic analysis as shown in Figure 7.5. Lurlenic acid (168) can be constructed from three building blocks,... 

Our synthesis of lurlenic acid (168) is summarized in Figure 7.6.4-6 The starting material A was half-protected and prenylated to give B, which was further protected and oxidized to furnish C. Wittig olefination... 

Takanashi, S.I., and K. Mori, Synthesis of Lurlenic Acid and Lurlenol, the Sex Pheromones of the Green Flagellate Chlamydomonas, Liebigs Ann./Recueil, 825-838 (1997). 

In addition to the several examples mentioned above, the syntheses of the following natural products and related compounds via Pd-catalyzed allylation have been reported, and they are summarized in Sect, in.2.18 ( )-neomanoalide, vineomycinone B2 methyl ester, cephalosporin analogs,hennoxazole stypoldione, 6-keto-prostanoids, constanolactones A and lurlene, lurlenic acid, and lurlennlJ " ... 

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