A Convenient Route to the Synthesis of Isotopomeric Dihydro-2(3H)furanones
2007
Frediani, P. | Rosi, L. | Frediani, M. | Bartolucci, G. | Bambagiotti-Alberti, M.
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 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.
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