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(5H)-one, isolated from plant-derived smoke, efficiently inhibits seed germination and significantly reduces the effect of the highly active germination promotor karrikinolide (KAR1, 3-methyl-2H-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(5H)-ones containing one and two 13C atoms for the identification of metabolic degradation products in order to provide insight into the mechanism of action.