作者:Piero Frediani、Luca Rosi、Marco Frediani、Gianluca Bartolucci、Massimo Bambagiotti-Alberti
DOI:10.1021/jf070305y
日期:2007.5.1
A general synthetic procedure leading to isotopomeric dihydro-2(3H)furanones (gamma-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 C-4 (succinic) or unsaturated diacids C-4 (fumaric, maleic, or acetylendicarboxylic) in the presence of Ru4H4(CO)(8)(PBu3)(4) using a deuterium pressure of 180 bar at 180 degrees 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'-D-6] (benzyl-protected matairesinol-D-6) was fully characterized.