Chemistry Letters, Vol.32, No.9, 844-845, 2003
Total synthesis of alpha-ketol derivative of linolenic acid (KODA), a flower-inducing factor in Lemna paucicostata
Racemic 9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienoic acid [(+/-)-KODA] was synthesized via a coupling reaction between a diyne and an epoxide derived from methyl oleate as a key step. An optically active 9R-KODA was also synthesized by enantioselective lipase-catalyzed esterification of an allyl alcohol. Both synthetic (+/-)-KODA and 9R-KODA showed remarkable flower-inducing activity in Pharbitis nil.