title: Highly Efficient and Practical Syntheses of Lavendamycin Methyl Ester and Related Novel Quinolindiones.
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.
authors.affiliation: Department of Chemistry, Ball State University, Muncie, Indiana 47306.
authors.forename: Mohammad
authors.initials: M
authors.lastname: Behforouz
authors.forename: Jalal
authors.initials: J
authors.lastname: Haddad
authors.forename: Wen
authors.initials: W
authors.lastname: Cai
authors.forename: Macklin B.
authors.initials: MB
authors.lastname: Arnold
authors.forename: Farahnaz
authors.initials: F
authors.lastname: Mohammadi
authors.forename: Aron C.
authors.initials: AC
authors.lastname: Sousa
authors.forename: Mark A.
authors.initials: MA
authors.lastname: Horn