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

28 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
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja992486t

Cite this

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

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,

day = "15",

doi = "10.1021/ja992486t",

language = "English (US)",

volume = "121",

pages = "11261--11266",

journal = "Journal of the American Chemical Society",

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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.

UR - https://www.scopus.com/pages/publications/0033572694

UR - https://www.scopus.com/pages/publications/0033572694#tab=citedBy

U2 - 10.1021/ja992486t

DO - 10.1021/ja992486t

M3 - Article

AN - SCOPUS:0033572694

SN - 0002-7863

VL - 121

SP - 11261

EP - 11266

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 49

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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