AN EFFICIENT SYNTHESIS OF 8-HYDROXY-6,7-DIMETHOXY-3-METHYLISOCOUMARIN-(6-O-METHYLRETICULOL)

Authors

  • Aamer Saeed Department of Chemistry, Quaid-I-Azam University 45320 Islamabad
  • Somia Ehsan Department of Chemistry, Quaid-I-Azam University 45320 Islamabad

DOI:

https://doi.org/10.1007/8137

Keywords:

endophytic fungus, isocoumarin, reticulol, 3, 4, 5-trimethoxyhomophthalic acid

Abstract

An efficient synthesis  of  8-hydroxy-6,7-dimethoxy-3-methylisocoumarin (6-O-methylreti-culol), a metabolite of several fungal species possessing phosphodiesterase inhibitor, topoisome-rase I inhibitor activities and antitumor efficacy, has been described. 3,4,5-Trimethoxyhomo-phthalic acid was refluxed with acetic anhydride  in dry pyridine and the resulting 2,3,4-tri-methoxy-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.

How to Cite
Saeed, A.; Ehsan, S. Chem. Heterocycl. Compd. 2005, 41, 1381. [Khim. Geterotsikl. Soedin. 2005, 1644.]

For this article in the English edition, see DOI 10.1007/s10593-006-0005-6

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Published

2023-10-16

Issue

No. 11 (2005)

Section

Original Papers