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Efficient and Practical Synthesis of a Potent Anti-MRSA β-Methylcarbapenem Containing a Releasable Side Chain

1999; American Chemical Society; Volume: 121; Issue: 49 Linguagem: Inglês

10.1021/ja992486t

1943-2984

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,

Pneumocystis jirovecii pneumonia detection and treatment

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.