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An efficient synthesis of 3,5‐dimethoxyhomophthalic acid, a key intermediate for synthesis of natural isocoumarins
Author(s) -
Saeed Aamer,
Rama Nasim H.,
Arfan M.
Publication year - 2003
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570400317
Subject(s) - isocoumarins , chemistry , carbonylation , formylation , isocoumarin , organic chemistry , condensation , bromide , rhodium , catalysis , combinatorial chemistry , carbon monoxide , physics , thermodynamics
3,5‐Dimethoxyhomophthalic acid was prepared efficiently in three steps, from 3,5‐dimethoxybenzyl bromide via rhodium‐catalyzed direct carbonylation to 3,5‐dimethoxyphenylacetic acid followed by successive o ‐formylation and oxidation. Isocoumarins related to agrimonolide and achlisocoumarin 1 were prepared in single step by condensation of the homophthalic acid with appropriate acid chlorides.