Preparation of the enantiomers of hydroxy-C18 fatty acids and their anti-rice blast fungus activities

In order to examine the correlation between the anti-rice blast fungus activity and the chirality or allylic alcohols 1-3, which were characterized from the infected rice plants as an enantiomeric mixture with < 10% e.e., a procedure for the chemical preparation of both enantiomers was explored, starting from the original fatty acids 4 and 5. The anti-rice blast fungus activities of both enantiomers of the allylic alcohols 1-3 and epoxy alpha -linolenic acids 12 and 13 demonstrate no noticeable correlation between the activity and chirality. (C) 2001 Elsevier Science Ltd. All rights reserved.