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


  • Josephine M Gießel Martin-Luther Universität Halle-Wittenberg
  • Tim Kohlmann Martin-Luther Universität Halle-Wittenberg
  • Tina Zeitz Martin-Luther Universität Halle-Wittenberg
  • Ralph Kluge Martin-Luther Universität Halle-Wittenberg
  • René Csuk Martin-Luther Universität Halle-Wittenberg



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.

Author Biography

René Csuk, Martin-Luther Universität Halle-Wittenberg

Organic ChemistryHead of Department


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Organic Chemistry