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

Josephine M Gießel, Tim Kohlmann, Tina Zeitz, Ralph Kluge, René Csuk
2019 Mediterranean Journal of Chemistry  
<p>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 <strong>1</strong> in the presence of Ru(dndp)<sub>3</sub>Cl<sub>2</sub> furnished in a [2+2] cycloaddition cyclobutanoid dimer, a d-truxinic acid. The putative mechanism of this reaction was supported by DFT calculations. <strong></strong></p>
doi:10.13171/mjc941911051057rc fatcat:rorbqy4aljgvzdqu5i5cogneei