Attachment of a styryl group to the 6-position of a protected penicillanic acid via cobaloxime-mediated radical alkyl-alkenyl cross coupling

William D. Detlefsen, Bruce Branchaud

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Cobaloxime-catalyzed cross coupling of styrene with 6α-bromopenicillanic acid pivalolyl-oxymethyl ester (4) introduces a styryl group into the 6 position of the penicillanic acid nucleus. The method should be capable of introducing a variety of aryl-substituted alkenes into the 6 position. Such compounds may be useful as novel β-lactam antibiotics/β-lactamase inhibitors.

Original languageEnglish (US)
Pages (from-to)2289-2292
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume6
Issue number19
DOIs
StatePublished - Oct 8 1996
Externally publishedYes

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Penicillanic Acid
Lactams
Styrene
Alkenes
Esters
Anti-Bacterial Agents
cobaloxime
brobactam

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

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abstract = "Cobaloxime-catalyzed cross coupling of styrene with 6α-bromopenicillanic acid pivalolyl-oxymethyl ester (4) introduces a styryl group into the 6 position of the penicillanic acid nucleus. The method should be capable of introducing a variety of aryl-substituted alkenes into the 6 position. Such compounds may be useful as novel β-lactam antibiotics/β-lactamase inhibitors.",
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AB - Cobaloxime-catalyzed cross coupling of styrene with 6α-bromopenicillanic acid pivalolyl-oxymethyl ester (4) introduces a styryl group into the 6 position of the penicillanic acid nucleus. The method should be capable of introducing a variety of aryl-substituted alkenes into the 6 position. Such compounds may be useful as novel β-lactam antibiotics/β-lactamase inhibitors.

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