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Original Articles

Synthesis and Potato Cell Expansion-inducing Activity of the Stereochemically Restricted Bicyclic Analogue of 7-Epi-jasmonic Acid

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Pages 2702-2705 | Received 05 Jun 2000, Accepted 11 Jul 2000, Published online: 22 May 2014

  • 1) Sembdner, G. and Parthier, B., The biochemistry and the physiological and molecular actions of jasmonates. Annu. Rev. Plant Physiol. Plant Mol. Biol., 44, 569-589 (1993) and references cited therein.
  • 2) Koda, Y., Kikuta, Y., Kitahara, T., Nishi, T., and Mori, K., Comparisons of various biological activities of stereoisomers of methyl jasmonate. Phytochemistry, 31, 1111-1114 (1992).
  • 3) Toshima, H., Nara, S., Ichihara, A., Koda, Y., and Kikuta, Y., Syntheses and potato tuber-inducing activity of coronafacic acid analogues. Biosci. Biotechnol. Biochem., 62, 681-688 (1998).
  • 4) Kiyota, H., Yoneta, Y., and Oritani, T., Synthesis and biological activities of methyl 3,7- and 4,5-didehydrojasmonates. Phytochemistry, 46, 983-986 (1997).
  • 5) Seto, H., Nomura, E., Fujioka, S., Koshino, H., Suenaga, T., and Yoshida, S., Easy preparation of methyl 7-epi-jasmonate and four stereoisomers of methyl cucurbate, and assessment of the stereogenic effect of jasmonate on phytohormonal activities. Biosci. Biotechnol. Biochem., 63, 361-367 (1999).
  • 6) Toshima, H., Aramaki, H., and Ichihara, A., Syntheses of stereochemically restricted lacton-type analogues of jasmonic acids. Biosci. Biotechnol. Biochem., 64, 1988-1992 (2000).
  • 7) Hashimoto, S., Shinoda, T., Shimada, Y., Honda, T., and Ikegami, S., Chiral synthesis of isocarbacyclin ((+)-9(0)-methano-Δ6(9α)-PGI1) intermediate via rhodium(II)-catalyzed intramolecular C-H insertion reaction. Tetrahedron Lett., 128, 637-640 (1987).
  • 8) Compound 6 was obtained as an inseparable mixture of diastereomers because racemic 2,3-butandiol containing ca. 5% of the meso form was used for acetalization.
  • 9) Scott, W. J. and Stille, J. K., Palladium-catalyzed coupling of vinyl triflates with organostannanes. Synthetic and mechanistic studies. J. Am. Chem. Soc., 108, 3033-3040 (1986).
  • 10) Compounds 8 and 9 were also obtained as an inseparable mixture of diastereomers.
  • 11) Takahashi, K., Fujino, K., Kikuta, Y., and Koda, Y., Expansion of potato cells in response to jasmonic acid. Plant Science, 100, 3-8 (1994).
  • 12) A mixture of minor (±)-1 (5%) and major (±)-2 (95%), which had been prepared from commercially available methyl (±)-jasmonate, was used as the JA standard for the bioassay.

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