Chlorination at the 8-Position of a Functionalized Quinolone and the Synthesis of Quinolone Antibiotic ABT-492
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- 作者：David M. Barnes ; Alan C. Christesen ; Kenneth M. Engstrom ; Anthony R. Haight ; Margaret C. Hsu ; Elaine C. Lee ; Matthew J. Peterson ; Daniel J. Plata ; Prasad S. Raje ; Eric J. Stoner ; Jason S. Tedrow ; Seble
- 刊名：Organic Process Research & Development
- 出版年：2006
- 出版时间：July 2006
- 年：2006
- 卷：10
- 期：4
- 页码：803 - 807
- 全文大小：103K
- 年卷期：v.10,no.4(July 2006)
- ISSN：1520-586X
文摘
The total synthesis of quinolone antibiotic ABT-492 has beenachieved in 67% yield over nine steps from 2,4,5-trifluorobenzoic acid. The highlights of this synthesis include a novelchemoselective chlorination at the 8-position of a highlyelaborated quinolone core. In addition, a Lewis acid promotedcyclization reaction to form the quinolone heterocycle wasdeveloped which was incorporated into a one-pot, three-stepcyclization/coupling/protection sequence that proceeds in 93%yield.