Syntheses of 3-Oxa-OPC and 2-Fluoro-OPC Homologues

Hiroaki TOSHIMA; Yumiko FUJINO; Akitami ICHIHARA; Yasunori KODA; Yoshio KIKUTA

doi:10.1271/bbb.62.689

Bioscience, Biotechnology, and Biochemistry

Online ISSN : 1347-6947
Print ISSN : 0916-8451

Organic Chemistry Regular Papers

Syntheses of 3-Oxa-OPC and 2-Fluoro-OPC Homologues

Hiroaki TOSHIMA, Yumiko FUJINO, Akitami ICHIHARA, Yasunori KODA, Yoshio KIKUTA

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Keywords: jasmonic acid, jasmonoid, octadecanoid, OPC, β-oxidation

JOURNAL FREE ACCESS

1998 Volume 62 Issue 4 Pages 689-694

DOI https://doi.org/10.1271/bbb.62.689

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Abstract

Synopsis: 3-Oxa-OPC and 2-fluoro-OPC homologues which do not undergo β-oxidation were synthesized from esters of odd-numbered OPC homologues by a short-step procedure. The 3-oxa-OPC homologues were synthesized via etherification of an alcohol with tert-butyl bromoacetate under phase-transfer conditions. The 2-fluoro-OPC homologues were synthesized via the addition of the trichloromethyl anion to an aldehyde and subsequent fluorination.

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