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

doi:10.1021/ja992486t

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

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	11261-11266
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	121
Issue number	49
DOIs	https://doi.org/10.1021/ja992486t
State	Published - Dec 15 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja992486t

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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

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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.",

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

year = "1999",

month = dec,

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doi = "10.1021/ja992486t",

language = "English (US)",

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T1 - Efficient and practical synthesis of a potent anti-MRSA β- methylcarbapenem containing a releasable side chain

AU - Humphrey, Guy R.

AU - Miller, Ross A.

AU - Pye, Philip J.

AU - Rossen, Kai

AU - Reamer, Robert A.

AU - Maliakal, Ashok

AU - Ceglia, Scott S.

AU - Grabowski, Edward J.J.

AU - Volante, R. P.

AU - Reider, Paul J.

PY - 1999/12/15

Y1 - 1999/12/15

N2 - 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.

AB - 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.

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JF - Journal of the American Chemical Society

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ER -

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

Abstract

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