Application of organolithium and related reagents in synthesis. Part 13. Synthetic strategies based on aromatic metallation. A concise regiospecific conversion of benzoic acids into 4-hydroxy-1-arylnaphthalenes

DOI: 10.1016/S0040-4020(01)80334-3

Source and publish data:

Tetrahedron p. 929 - 938 (1993)

Update date:2022-08-05

Topics: Synthesis Conversion Reagents Concise Regiospecific Organolithium Benzoic acids

Authors:

Epsztajn, Jan

Jozwiak, Andrzej

Szczesniak, Aleksandra K.

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Article abstract of DOI:10.1016/S0040-4020(01)80334-3

The synthesis of the 3-unsubstituted phthalides (5) and their conversion into 1-hydroxy-1-arylphthalans (8), very useful precursors of isobenzofurans (10) and subsequent cycloaddition of them to dimethyl acetylenedicarboxylate as a way of regiospecific transformation of benzoic acids into dimethyl 4-hydroxy-1-(2-methoxyphenyl)naphthalene-2,3-dicarboxylates (12) (biaryls highly substituted around the axis), is described.

Full text of DOI:10.1016/S0040-4020(01)80334-3

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