Preparation of optically active 15-epoxy-alpha-linolenic acids and their anti-rice blast fungus activities

Authors
Kato, T Nakai, T Ishimatu, T Hoshikawa, M Namai, T
Citation
T. Kato et al., Preparation of optically active 15-epoxy-alpha-linolenic acids and their anti-rice blast fungus activities, HETEROCYCLE, 52(3), 2000, pp. 1353
Citations number
6
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
52
Issue
3
Year of publication
2000
Database
ISI
SICI code
0385-5414(20000301)52:3<1353:POOA1A>2.0.ZU;2-O
Abstract
By the action of NBS in aq. DME, alpha-linolenic acid was oxidized to 15-br omo-16-hydroxy-alpha-linolenic acid in 35% conversion yield. The bromohydri n was treated with lipase-PS and vinyl acetate to give the resolved acetate and bromohydrin. (15S,16R)- and (15R,16S)-Epoxy-alpha-linolenic acids were prepared from the corresponding resolved products. A comparison of anti-ri ce blast fungus activities showed that an unnatural epoxide is stronger tha n the natural epoxide.