A Convenient Synthesis of 3-Methoxyphthalic Anhydride
- 1 January 1975
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 5 (6) , 457-460
- https://doi.org/10.1080/00397917508065581
Abstract
Many antibiotics of the anthracycline family1 possess structures for which 3-methoxyphthalic anhydride (1) would be a suitable synthon2 in a total synthesis. A classic synthesis of (1) has employed 3-nitrophthalic acid3 but, in our hands, proceeded in low overall yield. Recent syntheses have utilized the Diels Alder reaction of dimethyl acetylenedicarboxylate (2) with 1-methoxy-1,3-cyclohexadiene,4 1,4-diacetoxybutadiene,5 2-acetoxyfuran,6 2-methoxyfuran7 or furan8 to obtain 3-hydroxyphthalic acid or a derivative. We now wish to report a convenient Diels-Alder synthesis of (1) from 3-methoxy-2-pyrone (3).Keywords
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