Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Organic Chemistry Notes
Synthesis and Potato Cell Expansion-inducing Activity of the Stereochemically Restricted Bicyclic Analogue of 7-Epi-jasmonic Acid
Hiroaki TOSHIMAShinji NARAYumiko FUJINOAkitami ICHIHARA
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JOURNAL FREE ACCESS

2000 Volume 64 Issue 12 Pages 2702-2705

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Abstract

  The stereochemically restricted bicyclic analogue of 7-epi-jasmonic acid was synthesized from a known bicyclo[3.3.0]octane derivative. The enol triflate derived from the bicyclic compound was subjected to palladium-catalyzed coupling with allyltributyltin to give the desired carbon skeleton. Selective catalytic hydrogenation and subsequent acidic hydrolysis gave a new bicyclic analogue of 7-epi-jasmonic acid. The ACC conjugate of the bicyclic analogue was also synthesized. This ACC conjugate exhibited only slightly weaker potato cell expansion-inducing activity than that of the JA standard.

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© 2000 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
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