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Application of a novel directing effect in an organocopper/orthoester reaction to the synthesis of deuterium labeled unsaturated esters

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Svatoš,  Aleš
Research Group Mass Spectrometry, MPI for Chemical Ecology, Max Planck Society;

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Citation

Shattuck, J. C., Svatoš, A., Blazey, C. M., & Meinwald, J. (1997). Application of a novel directing effect in an organocopper/orthoester reaction to the synthesis of deuterium labeled unsaturated esters. Tetrahedron Letters, 38(39), 6803-6806. doi:10.1016/S0040-4039(97)01599-2.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0012-B41C-6
Abstract
A new short and highly flexible pathway to derivatives 3a-d and 5 dihydro-12-oxo-phytodienoic acid, using an electrochemical CC bond coupling in an one-step procedure, is described. Jasmonic acid can be coupled with carboxylic acids in a mixed Kolbe electrolysis in acceptable yields. Functional groups are tolerated and, hence, the method offers a simple route to the title compounds which are otherwise difficult to prepare.