A practical and efficient preparation of the releasable naphthosultam side chain of a novel anti-MRSA carbapenem

Ross A. Miller, Guy R. Humphrey, David R. Lieberman, Scott S. Ceglia, Derek J. Kennedy, Edward J.J. Grabowski, Paul J. Reider

Research output: Contribution to journalArticle

40 Scopus citations

Abstract

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 languageEnglish (US)
Pages (from-to)1399-1406
Number of pages8
JournalJournal of Organic Chemistry
Volume65
Issue number5
DOIs
StatePublished - Mar 10 2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Miller, R. A., Humphrey, G. R., Lieberman, D. R., Ceglia, S. S., Kennedy, D. J., Grabowski, E. J. J., & Reider, P. J. (2000). A practical and efficient preparation of the releasable naphthosultam side chain of a novel anti-MRSA carbapenem. Journal of Organic Chemistry, 65(5), 1399-1406. https://doi.org/10.1021/jo991490k