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

doi:10.1021/jo991490k

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 journal › Article › peer-review

43 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 language	English (US)
Pages (from-to)	1399-1406
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	65
Issue number	5
DOIs	https://doi.org/10.1021/jo991490k
State	Published - Mar 10 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo991490k

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

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.",

author = "Miller, \{Ross A.\} and Humphrey, \{Guy R.\} and Lieberman, \{David R.\} and Ceglia, \{Scott S.\} and Kennedy, \{Derek J.\} and Grabowski, \{Edward J.J.\} and Reider, \{Paul J.\}",

year = "2000",

month = mar,

day = "10",

doi = "10.1021/jo991490k",

language = "English (US)",

volume = "65",

pages = "1399--1406",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - A practical and efficient preparation of the releasable naphthosultam side chain of a novel anti-MRSA carbapenem

AU - Miller, Ross A.

AU - Humphrey, Guy R.

AU - Lieberman, David R.

AU - Ceglia, Scott S.

AU - Kennedy, Derek J.

AU - Grabowski, Edward J.J.

AU - Reider, Paul J.

PY - 2000/3/10

Y1 - 2000/3/10

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0034629332

UR - https://www.scopus.com/inward/citedby.url?scp=0034629332&partnerID=8YFLogxK

U2 - 10.1021/jo991490k

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VL - 65

SP - 1399

EP - 1406

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

ER -

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

Abstract

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