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Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet
- Plant oxylipins are an important class of signaling molecules in plants. The cyclic adducts of epinephrine or norepinephrine with the naturally occurring oxylipin (12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid (KODA, 1) or its synthetic analogues (2-6) have been reported to possess flower-inducing activity toward Lemna paucicostata. By in vivo and in vitro experiments with seedlings of Pharbitis nil cv. Violet carbonyl groups of the alpha-ketols (1 and 3) and the ketones (7 and 9) were enantio-selectively reduced to give their corresponding vicinal diols (2 and 4) and alcohols (8 and 10). The stereochemistry at the oxymethine carbon was determined based on the long range C H coupling constants and the modified Mosher's method. Orientation of the adjacent hydroxyl group in (1 and 3) did not affect the enantio-selectivity, whereas the conversion was slightly affected and higher yields were obtained with the R-enantiomers of the alpha-ketols.
Author details: | Ariaki Murata, Kenji Kai, Ken Tsutsui, Jun Takeuchi, Yasushi Todoroki, Kazuo Furihata, Mineyuki Yokoyama, Susanne BaldermannORCiDGND, Naoharu Watanabe |
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DOI: | https://doi.org/10.1016/j.tet.2012.04.077 |
ISSN: | 0040-4020 |
Title of parent work (English): | Tetrahedron |
Publisher: | Elsevier |
Place of publishing: | Oxford |
Publication type: | Article |
Language: | English |
Year of first publication: | 2012 |
Publication year: | 2012 |
Release date: | 2017/03/26 |
Tag: | Enantio-selective reduction; Flowering; Lemna paucicostata; Oxylipins; Pharbitis nil cv. Violet |
Volume: | 68 |
Issue: | 27-28 |
Number of pages: | 7 |
First page: | 5583 |
Last Page: | 5589 |
Funding institution: | Research and Development Program for New Bioindustry Initiatives |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Ernährungswissenschaft |
Peer review: | Referiert |