Chlorination at the 8-Position of a Functionalized Quinolone and the Synthesis of Quinolone Antibiotic ABT-492

The total synthesis of quinolone antibiotic ABT-492 has been achieved in 67% yield over nine steps from 2,4,5-trifluorobenzoic acid. The highlights of this synthesis include a novel chemoselective chlorination at the 8-position of a highly elaborated quinolone core. In addition, a Lewis acid promote...

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Published inOrganic process research & development Vol. 10; no. 4; pp. 803 - 807
Main Authors Barnes, David M, Christesen, Alan C, Engstrom, Kenneth M, Haight, Anthony R, Hsu, Margaret C, Lee, Elaine C, Peterson, Matthew J, Plata, Daniel J, Raje, Prasad S, Stoner, Eric J, Tedrow, Jason S, Wagaw, Seble
Format Journal Article
LanguageEnglish
Published American Chemical Society 21.07.2006
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Summary:The total synthesis of quinolone antibiotic ABT-492 has been achieved in 67% yield over nine steps from 2,4,5-trifluorobenzoic acid. The highlights of this synthesis include a novel chemoselective chlorination at the 8-position of a highly elaborated quinolone core. In addition, a Lewis acid promoted cyclization reaction to form the quinolone heterocycle was developed which was incorporated into a one-pot, three-step cyclization/coupling/protection sequence that proceeds in 93% yield.
ISSN:1083-6160
1520-586X
DOI:10.1021/op0600557