TY - JOUR
T1 - Synthesis and plant growth inhibitory activity of both enantiomers of pyricuol, a phytotoxin isolated from rice blast disease fungus Magnaporthe grisea
AU - Tanaka, Koji
AU - Nakamura, Yoko
AU - Sasaki, Ayaka
AU - Ueda, Rumi
AU - Suzuki, Yuji
AU - Kuwahara, Shigefumi
AU - Kiyota, Hiromasa
N1 - Funding Information:
We thank Prof. Jin-Keol Kim (KRICT, Korea) for providing the natural sample of pyricuol, and Prof. Manabu Nukina (Yamagata University, Japan) for giving the useful information about foliar application assay. We also appreciate the assistance of Mrs. Teiko Yamada (Tohoku Univ.) for measuring NMR and mass spectra. Financial supports by grant-in-aid from Japan Society for the Promotion of Science (No. 17580092 and 19580120), The Agricultural Chemical Research Foundation, Intelligent Cosmos Foundation, and The Naito Foundation is gratefully acknowledged.
PY - 2009/8/1
Y1 - 2009/8/1
N2 - Both enantiomers and racemate of pyricuol, a phytotoxin isolated from the rice blast disease fungus, Magnaporthe grisea, have been synthesized by using Stille coupling and [2,3]-Wittig rearrangement reactions as the key steps. Both enantiomers induced dark necrotic lesions on rice leaves almost equally, but did not affect the growth of rice second leaf sheath and the germination of lettuce. Only natural enantiomer promoted the root growth of rice and lettuce.
AB - Both enantiomers and racemate of pyricuol, a phytotoxin isolated from the rice blast disease fungus, Magnaporthe grisea, have been synthesized by using Stille coupling and [2,3]-Wittig rearrangement reactions as the key steps. Both enantiomers induced dark necrotic lesions on rice leaves almost equally, but did not affect the growth of rice second leaf sheath and the germination of lettuce. Only natural enantiomer promoted the root growth of rice and lettuce.
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U2 - 10.1016/j.tet.2009.05.052
DO - 10.1016/j.tet.2009.05.052
M3 - Article
AN - SCOPUS:67649370764
SN - 0040-4020
VL - 65
SP - 6115
EP - 6122
JO - Tetrahedron
JF - Tetrahedron
IS - 31
ER -