A convenient route to the synthesis of isotopomeric dihydro-2(3H)furanones.
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 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'-D6] (benzyl-protected matairesinol-D6) was fully characterized.
Frediani
Piero
P
Department of Organic Chemistry, University of Florence, Sesto, Italy. piero.frediani@unifi.it
Rosi
Luca
L
Frediani
Marco
M
Bartolucci
Gianluca
G
Bambagiotti-Alberti
Massimo
M
D015107:4-Butyrolactone / Q000737:chemistry*; D003903:Deuterium; D005650:Fumarates / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis*; D007553:Isotope Labeling / Q000379:methods*; D017705:Lignans / Q000138:chemical synthesis*; D008298:Maleates / Q000737:chemistry; D012428:Ruthenium; D019802:Succinic Acid / Q000737:chemistry
D005650:Fumarates; D005663:Furans; D017705:Lignans; D008298:Maleates; C068935:matairesinol; D012428:Ruthenium; C032005:fumaric acid; C030272:maleic acid; D019802:Succinic Acid; D003903:Deuterium; D015107:4-Butyrolactone