Synthesis, Absolute Configuration and Biological Activity of Both Enantiomers of 2-(5,6-Dichloro-3-indolyl)propionic Acid: New Dichloroindole Auxins.

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  • KATAYAMA Masato
    Department of Chemistry, National Industrial Research Institute of Nagoya(NIRIN)
  • KATO Yasuhito
    Ageo & Fine Chemicals Research Laboratory, Nippon Kayaku Co. Ltd.
  • MARUMO Shingo
    Graduate School of Bioagricultural Sciences, Nagoya University

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Racemic 2-(5,6-dichloro-3-indolyl)propionic acid (5,6-Cl2-2-IPA) was synthesized from 5,6-dichloro-indole-3-acetic acid (5,6-Cl2-IAA) by successive esterification, methoxycarbonylation, methylation, and double hydrolysis. The racemate was converted to the diastereomeric esters of (S)-(−)-1-phenylethyl alcohol. These were separated by HPLC into two optically active diastereomers and then hydrolyzed with p-TsOH to the optically active enantiomers of 5,6-Cl2-2-IPA. The absolute configurations of both the 5,6-Cl2-2-IPA enantiomers were determined by comparing the 1H-NMR spectra of their diastereomeric (S)-(−)-1-phenylethyl esters with those of the diastereomeric (S)-(−)-1-phenylethyl esters of 2-(3-indolyl)propionic acid (2-IPA) whose absolute configurations are already known.<br> There was no essential difference between (S)-(+)- and (R)-(−)-5,6-Cl2-2-IPA in hypocotyl growth-inhibiting activity toward Chinese cabbage, but their inhibitory activities were stronger than that of the potent mother auxin, 5,6-Cl2-IAA. No essential difference in the coleoptile elongating activity of Avena sativa was apparent for the enantiomers, this activity being about one-third that of 5,6-Cl2-IAA.

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