Highly Efficient and Practical Syntheses of Lavendamycin Methyl Ester and Related Novel Quinolindiones |
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Authors: | Behforouz Mohammad Haddad Jalal Cai Wen Arnold Macklin B. Mohammadi Farahnaz Sousa Aron C. Horn Mark A. |
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Affiliation: | Department of Chemistry, Ball State University, Muncie, Indiana 47306. |
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Abstract: | The novel 7-(N-formyl-, 7-(N-acetyl-, and 7-(N-isobutyrylamino)-2-methylquinoline-5,8-diones were synthesized in excellent overall yields in three steps via the nitration of the commercially available 8-hydroxy-2-methylquinoline followed by a reduction-acylation step and then oxidation. Acid hydrolysis of 7-(N-acetylamino)-2-methylquinoline-5,8-dione (14a) afforded the novel 7-aminoquinoline-5,8-dione 7 in excellent yields. Due to our efficient preparation of dione 14a, we now report a short and practical method for the total synthesis of the potent antitumor agent lavendamycin methyl ester (1b) with an excellent overall yield. |
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