Synthesis and plant growth inhibitory activity of both enantiomers of pyricuol, a phytotoxin isolated from rice blast disease fungus Magnaporthe grisea

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 equa...

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Bibliographic Details
Published in:Tetrahedron 2009-08, Vol.65 (31), p.6115-6122
Main Authors: Tanaka, Koji, Nakamura, Yoko, Sasaki, Ayaka, Ueda, Rumi, Suzuki, Yuji, Kuwahara, Shigefumi, Kiyota, Hiromasa
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
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Summary: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. Both enantiomers and racemate of pyricuol, a phytotoxin isolated from the rice blast disease fungus, M. 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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.05.052