K. Kobayashi et al., A SIMPLE METHOD FOR THE SYNTHESIS OF 4-ARYL-9-OXYNAPHTHOFURANONE LIGNANS, Journal of the Chemical Society. Perkin transactions. I, (4), 1997, pp. 443-446
The 9-aryl-4-oxynaphthofuran-1(3H)-one system is generally synthesized
in two steps from alpha-aryl-o-toluic acid derivatives. The method in
volves a tandem conjugate addition-Dieckmann type condensation between
alpha-lithiated alpha-aryl-o-toluic acid derivatives and 2-furan-2(5H
)-one as a key step followed by simple dehydrogenation or dehydration,
and can be applied to the synthesis of two natural lignans (neojustic
idin A and neojusticidin B).