Efficient and practical synthesis of a potent anti-MRSA β- methylcarbapenem containing a releasable side chain

Guy R. Humphrey, Ross A. Miller, Philip J. Pye, Kai Rossen, Robert A. Reamer, Ashok Maliakal, Scott S. Ceglia, Edward J.J. Grabowski, R. P. Volante, Paul J. Reider

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27 Scopus citations

Abstract

We describe a convergent synthesis of the MRSA β-methyl carbapenem 1, wherein the molecule is assembled from the naphthosultam side chain 2 and the allylic carbonate of the β-Me carbapenem piece 6. The β-Me stereochemistry of 6 is set up in a novel titanium enolate addition into the TBDMS acetoxy azetidinone 5. The benzenesulfonate salt of 1 is endowed with exceptional stability.

Original languageEnglish (US)
Pages (from-to)11261-11266
Number of pages6
JournalJournal of the American Chemical Society
Volume121
Issue number49
DOIs
StatePublished - Dec 15 1999
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Humphrey, G. R., Miller, R. A., Pye, P. J., Rossen, K., Reamer, R. A., Maliakal, A., Ceglia, S. S., Grabowski, E. J. J., Volante, R. P., & Reider, P. J. (1999). Efficient and practical synthesis of a potent anti-MRSA β- methylcarbapenem containing a releasable side chain. Journal of the American Chemical Society, 121(49), 11261-11266. https://doi.org/10.1021/ja992486t