Highly Efficient and Practical Syntheses of Lavendamycin Methyl Ester and Related Novel Quinolindiones

Autor:	Aron Sousa, Jalal Haddad, Macklin B. Arnold, Mohammad Behforouz, Wen Cai, Farahnaz Mohammadi, Mark A. Horn
Rok vydání:	1996
Předmět:	Antitumor activity chemistry.chemical_compound Chemistry Nitration Yield (chemistry) Organic Chemistry Total synthesis Acid hydrolysis Lavendamycin Combinatorial chemistry
Zdroj:	The Journal of Organic Chemistry. 61:6552-6555
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo960794t
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::77b820f18869df34c00a0c859537cf3a https://doi.org/10.1021/jo960794t Zobrazit plný text záznamu