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Synthesis of sinapine and its unprecedented ruthenium-catalyzed [2+2] photodimerization

Josephine M Gießel, Tim Kohlmann, Tina Zeitz, Ralph Kluge, René Csuk

Abstract


Sinapine was easily synthesized from commercially available starting materials in an overall yield of 32% while 0.47% were obtained by its extraction from white mustard. Irradiation of 1 in the presence of Ru(dndp)3Cl2 furnished in a [2+2] cycloaddition cyclobutanoid dimer, a d-truxinic acid. The putative mechanism of this reaction was supported by DFT calculations.


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DOI: http://dx.doi.org/10.13171/mjc941911051057rc

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