35 単細胞緑鞭毛藻Chlamydomonas allensworthiiの性フェロモンであるラーレン及びラーレノールの合成(口頭発表の部)
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The green flagellate Chlamydomonas eugametos and its sexuality were extensively studied by Moewus and Kuhn in 1930's to 1950's, whose work later turned out to be a scientific fraud. In 1995, two sex pheromones produced by female gametes of Chlamydomonas allensworthii were isolated and identified as lurlenic acid 1 and lurlenol 2 by Starr, Jaenicke and Marner. Here we report the first synthesis of 1 and 2. 1) First approach to lurlenic acid 1: Our first route to synthesize lurlenic acid included a palladium-catalyzed reaction as the key step, starting from commercially available geranylgeraniol, 2,3-dimethyl-p-hydroquinone and D-xylose. This synthesis gave an inseparable mixture of two compounds, lurlenic acid and its (12Z)-isomer due to the isomerization in the course of the palladium-catalyzed coupling step. This mixture was as bioactive as the natural product. 2) Second approach to lurlenic acid 1: In the second synthetic attempt, a sulfone-coupling was the key step to synthesize lurlenic acid as the only product without isomerization of the double bond at C-12. Our starting materials were farnesol, 2,3-dimethyl-p-hydroquinone and D-xylose. ^1H- and ^<13>C-NMR spectra of the synthetic lurlenic acid were identical with those of the natural product. 3) Synthesis of lurlenol 2: Lurlenol was synthesized in a similar manner. Its ^1H- and ^<13>C-NMR data were identical with those of the natural product. 4) Synthesis of compound 3: We also synthesized the compound 3 which might be the biosynthetic precursor of the two pheromones. Bioactivity of this compound is now being tested.
- 天然有機化合物討論会の論文
- 1996-09-02
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