Treatment of methyl 12-hydroxypodocarpa-8,11,13-trien-19-oate (5) with
a commercial sample of thallium(III) trifluoroacetate gave a low yiel
d (5%) of a non-symmetric ether-linked dimer (15). Use of freshly prep
ared thallium(III) trifluoroacetate gave a 28% yield of the symmetrica
l biaryl dimer (16). The dimethyl ether (17) was prepared in low yield
(10%) by treatment of methyl 12-methoxypodocarpa-8,11,13-trien-19-oat
e (4) with the latter reagent.