APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESIS - PART21 - SYNTHETIC STRATEGIES BASED ON ORTHO-AROMATIC METALATION - A CONCISE REGIOSPECIFIC SYNTHESIS OF ARYLNAPHTHALANES AS PRECURSORS OF NAPHTHYLISOQUINOLINE ALKALOIDS
J. Epsztajn et al., APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESIS - PART21 - SYNTHETIC STRATEGIES BASED ON ORTHO-AROMATIC METALATION - A CONCISE REGIOSPECIFIC SYNTHESIS OF ARYLNAPHTHALANES AS PRECURSORS OF NAPHTHYLISOQUINOLINE ALKALOIDS, Journal of the Chemical Society. Perkin transactions. I (Print), (16), 1998, pp. 2563-2567
A novel procedure is described for synthesising regioselectively subst
ituted biaryls such as 12. It involves converting phthalides 4, via cy
cloaddition of dimethyl acetylenedicarboxylate to 1-arylisobenzofurans
6, into dimethyl 1-arylnaphthalene-2,3-dicarboxylates 8, which upon h
ydrolytic decarboxylation give lactones 11 and then esters 12.