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An Efficient Synthesis of 8-Hydroxy-6,7-dimethoxy-3-methylisocoumarin (6-O-methylreticulol)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

An efficient synthesis of 8-hydroxy-6,7-dimethoxy-3-methylisocoumarin (6-O-methylreticulol), a metabolite of several fungal species possessing phosphodiesterase inhibitor, topoisomerase I inhibitor activities and antitumor efficacy, has been described. 3,4,5-Trimethoxyhomophthalic acid was refluxed with acetic anhydride in dry pyridine and the resulting 2,3,4-trimethoxy-6-(2-oxopropyl)benzoic acid was smoothly cyclodehydrated to 6,7,8-trimethoxy-3-methylisocoumarin using acetic anhydride. Regioselective demethylation of the latter yielded the 6-O-methylreticulol.

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Authors and Affiliations

  1. Department of Chemistry, Quaid-I-Azam University, 45320, Islamabad, Pakistan

    Aamer Saeed & Somia Ehsan

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  1. Aamer Saeed
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  2. Somia Ehsan
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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1644–1648, November, 2005.

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Saeed, A., Ehsan, S. An Efficient Synthesis of 8-Hydroxy-6,7-dimethoxy-3-methylisocoumarin (6-O-methylreticulol). Chem Heterocycl Compd 41, 1381–1385 (2005). https://doi.org/10.1007/s10593-006-0005-6

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  • DOI: https://doi.org/10.1007/s10593-006-0005-6

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