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