TY  - JOUR
A1  - Murata, Ariaki
A1  - Kai, Kenji
A1  - Tsutsui, Ken
A1  - Takeuchi, Jun
A1  - Todoroki, Yasushi
A1  - Furihata, Kazuo
A1  - Yokoyama, Mineyuki
A1  - Baldermann, Susanne
A1  - Watanabe, Naoharu
T1  - Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet
JF  - Tetrahedron
N2  - 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.
KW  - Enantio-selective reduction
KW  - Lemna paucicostata
KW  - Flowering
KW  - Oxylipins
KW  - Pharbitis nil cv. Violet
Y1  - 2012
U6  - https://doi.org/10.1016/j.tet.2012.04.077
SN  - 0040-4020
VL  - 68
IS  - 27-28
SP  - 5583
EP  - 5589
PB  - Elsevier
CY  - Oxford
ER  -