Synthesis, absolute configuration and biological activity of both enantiomers of 2-(5,6-dichloro-3-indolyl)propionic acid: New dichloroindole auxins

Article abstract of DOI:10.1271/bbb.65.270

Racemic 2-(5,6-dichloro-3-indolyl)propionic acid (5,6-Cl₂-2-IPA) was synthesized from 5,6-dichloroindole-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-Z-IPA. The absolute configurations of both the 5,6-CI₂-Z-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. 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.

Full text of DOI:10.1271/bbb.65.270

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Synthesis, Absolute Configuration and Biological
Activity of Both Enantiomers of 2-(5,6-Dichloro-3-
indolyl)propionic Acid: New Dichloroindole Auxins
Masato KATAYAMAa, Yasuhito KATOb & Shingo MARUMOc
a Department of Chemistry, National Industrial Research Institute of Nagoya(NIRIN)
b Ageo & Fine Chemicals Research Laboratory, Nippon Kayaku Co. Ltd.
c Graduate School of Bioagricultural Sciences, Nagoya University
Published online: 22 May 2014.
To cite this article: Masato KATAYAMA, Yasuhito KATO & Shingo MARUMO (2001) Synthesis, Absolute Configuration and
Biological Activity of Both Enantiomers of 2-(5,6-Dichloro-3-indolyl)propionic Acid: New Dichloroindole Auxins, Bioscience,
Biotechnology, and Biochemistry, 65:2, 270-276, DOI: 10.1271/bbb.65.270
To link to this article: http://dx.doi.org/10.1271/bbb.65.270
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