Highly efficient and practical syntheses of lavendamycin methyl ester and related novel quinolindiones

M Behforouz, J Haddad, W Cai, MB Arnold…

Index: Behforouz, Mohammad; Haddad, Jalal; Cai, Wen; Arnold, Macklin B.; Mohammadi, Farahnaz; Sousa, Aron C.; Horn, Mark A. Journal of Organic Chemistry, 1996 , vol. 61, # 19 p. 6552 - 6555

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Citation Number: 59

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 ...