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Stereoselective syntheses of two constituents against rice blast disease

✍ Scribed by Wu Wen-Lian; wu Yu-Lin

Publisher: Elsevier Science
Year: 1992
Tongue: French
Weight: 215 KB
Volume: 33
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)74811-8

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✦ Synopsis

llS,12S,13S)-Trihydroxy-(9Z,l5Z)-octadecadienoi~ acid 1 and methyl (11R,12S,13S)-ll-hydroxy-l2,l3-epoxy octadecadienoate 3a were synthesized starting from L-(+1-and D-t-)-tartaric acids, respectively. Oxygenated metabolites of unsaturated fatty acids play various important roles in biological systems, either in animals or in plants. Recently, several oxygenated C,, fatty acids have been isolated from rice plants such as Fukuyuki , suffering from the rice blast diseasel, among these acids, A-f can act as self-defense substances against the fungus.

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85 (12) , 81 (13), 75 (loo), 73 (84). Anal. calc. for CI5H2,O5Si (316.5): C 56.93, H 8.92, Si 8.87; found: C 56.79, H 8.82, Si 8.77. ## (I R.2S.3 S,4S)-I-[ ( tert-Butyl)dimethylsilyloxyjtetrahydro-2,3-(isopropylidenedioxy/-4-f ( Z/-pent-T-enyI]furan ((+)-7). Dropwise, a 15 % (Me,Si),NK soh. in t