@article{MurataKaiTsutsuietal.2012,
  author    = {Murata, Ariaki and Kai, Kenji and Tsutsui, Ken and Takeuchi, Jun and Todoroki, Yasushi and Furihata, Kazuo and Yokoyama, Mineyuki and Baldermann, Susanne and Watanabe, Naoharu},
  title     = {Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet},
  series = {Tetrahedron},
  volume    = {68},
  journal   = {Tetrahedron},
  number    = {27-28},
  publisher = {Elsevier},
  address   = {Oxford},
  issn      = {0040-4020},
  doi       = {10.1016/j.tet.2012.04.077},
  pages     = {5583 -- 5589},
  year      = {2012},
  abstract  = {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.},
  language  = {en}
}