Synthesis of a 13 C-labelled seed-germination inhibitor (3,4,5-trimethylfuran-2(5 H )-one) for the mode of action elucidation

It has been found that the butenolide 3,4,5-trimethylfuran-2(5 H )-one, isolated from plant-derived smoke, efficiently inhibits seed germination and significantly reduces the effect of the highly active germination promotor karrikinolide (KAR 1 , 3-methyl-2 H -furo[2,3- c ]pyran-2-one), another smoke-derived compound. This paper reports the synthesis of stable isotope-labelled 3,4,5-trimethylfuran-2(5 H )-ones containing one and two 13 C atoms for the identification of metabolic degradation products in order to provide insight into the mechanism of action. Graphical abstract