180208-55-3Relevant academic research and scientific papers
Highly efficient and practical syntheses of lavendamycin methyl ester and related novel quinolindiones
Behforouz, Mohammad,Haddad, Jalal,Cai, Wen,Arnold, Macklin B.,Mohammadi, Farahnaz,Sousa, Aron C.,Horn, Mark A.
, p. 6552 - 6555 (1996)
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.
