A convenient route to the synthesis of isotopomeric dihydro-2(3H)furanones

A general synthetic procedure leading to isotopomeric dihydro-2(3H)furanones (γ-butyrolactones) containing two, four, or six deuterium atoms has been developed. The labeled dihydro-2(3H)furanones were synthesized in quantitative yield from the saturated diacid C4 (succinic) or unsaturated diacids C4 (fumaric, maleic, or acetylendicarboxylic) in the presence of Ru4H4(CO)8(PBu3)4 using a deuterium pressure of 180 bar at 180 °C. This methodology was applied to the total synthesis of a hexadeuterated matairesinol lignan:  The 3,4-bis{[3-methoxy-4-(phenylmethoxy)phenyl]methyl}dihydro-2(3H)furanone-[7,7‘,8,8‘,9‘,9‘-D6] (benzyl-protected matairesinol-D6) was fully characterized. Keywords: Dihydro-2(3H)furanone; deuteration; ruthenium; catalyst; synthesis; isotope labeling; lignan