A practical large-scale synthesis of the naphthosultam-based side chain of the anti-MRSA antibiotic 1 has been achieved in 29% overall yield over seven steps from 1-methylnaphthalene. The synthesis was completed without the use of protecting groups, featuring a novel naphthosultam annelation, a chemoselective acid-catalyzed triflation, and the use of a novel naphthosultam dianion to effect functionalization through benzylic metalation.
|Original language||English (US)|
|Number of pages||8|
|Journal||Journal of Organic Chemistry|
|State||Published - Mar 10 2000|
All Science Journal Classification (ASJC) codes
- Organic Chemistry