Title

Total Synthesis of α-Ketol Derivative of Linolenic Acid (KODA), a Flower-inducing Factor in Lemna paucicostata.

Authors

Yokokawa, Yoshihiro; Kobayashi, Kouji; Yokoyama, Mineyuki; Yamamura, Shosuke

Abstract

Racemic 9-hydroxy-10-oxo-12(Z),l5(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.

Subjects

TARTARIC acid; ASYMMETRIC synthesis; EPOXY compounds; EPOXY resins; ETHERS; METHYL groups; OLEATES; JAPANESE morning glory

Publication

Chemistry Letters, 2003, Vol 32, Issue 9, p844

ISSN

0366-7022

Publication type

Academic Journal

DOI

10.1246/cl.2003.844