Homologues of dihydro-12-oxo-phytodienoic acid and jasmonic acid by mixed kolbe electrolysis

作者: Kerstin Schierle , Jörn Hopke , Marie-Luise Niedt , Wilhelm Boland , Eberhard Steckhan

DOI: 10.1016/S0040-4039(96)02012-6

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摘要: Abstract A new short and highly flexible pathway to derivatives 3a-d 5 dihydro-12-oxo-phytodienoic acid, using an electrochemical CC bond coupling in one-step procedure, is described. Jasmonic acid can be coupled with carboxylic acids a mixed Kolbe electrolysis acceptable yields. Functional groups are tolerated and, hence, the method offers simple route title compounds which otherwise difficult prepare.

参考文章(18)
Tatsumi Yamazaki, Kazuo Matsuda, Hiroshi Sugiyama, Shuichi Seto, Naotaka Yamaoka, Steric and electrostatic effects on the elimination of 2- and 3-sulphonyloxy-groups from methyl 4,6-O–benzylidenehexopyranosides J. Chem. Soc., Perkin Trans. 1. ,vol. 8, pp. 1981- 1984 ,(1977) , 10.1039/P19770001981
Bruno Klotz-Berendes, Hans J. Schäfer, Matthias Grehl, Roland Fröhlich, Diastereoselective Coupling of Anodically Generated Radicals Bearing Chiral Amide Groups Angewandte Chemie International Edition in English. ,vol. 34, pp. 189- 191 ,(1995) , 10.1002/ANIE.199501891
Jochen Knolle, Hans J. Schäfer, Synthese von Brevicomin durch Kolbe-Elektrolyse † Angewandte Chemie. ,vol. 87, pp. 777- 777 ,(1975) , 10.1002/ANGE.19750872110
Hans-Jürgen Schäfer, Recent contributions of kolbe electrolysis to organic synthesis Electrochemistry IV. ,vol. 152, pp. 91- 151 ,(1990) , 10.1007/BFB0034365
M. Saniewski, J. Czapski, Stimulatory effect of methyl jasmonate on the ethylene production in tomato fruits Cellular and Molecular Life Sciences. ,vol. 41, pp. 256- 257 ,(1985) , 10.1007/BF02002624
R.G. Woolford, THE ELECTROLYSIS OF ω-BROMOCARBOXYLIC ACIDS Canadian Journal of Chemistry. ,vol. 40, pp. 1846- 1850 ,(1962) , 10.1139/V62-280
Jochen Knolle, Hans J. Schäfer, Synthesis of Brevicomin by Kolbe Electrolysis Angewandte Chemie. ,vol. 14, pp. 758- 758 ,(1975) , 10.1002/ANIE.197507581
R. G. Woolford, W. Arbic, Ann Rosser, THE ELECTROLYSIS OF ω-BROMOCARBOXYLIC ACIDS: II. PREPARATION OF LONG-CHAIN ω-BROMOCARBOXYLIC ESTERS BY MIXED COUPLING REACTIONS Canadian Journal of Chemistry. ,vol. 42, pp. 1788- 1791 ,(1964) , 10.1139/V64-270