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 P. Branchaud

doi:10.1016/0960-894X(96)00415-5

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 P. Branchaud

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

1 Scopus citations

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 language	English (US)
Pages (from-to)	2289-2292
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	6
Issue number	19
DOIs	https://doi.org/10.1016/0960-894X(96)00415-5
State	Published - Oct 8 1996
Externally published	Yes

ASJC Scopus subject areas

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

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10.1016/0960-894X(96)00415-5

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

Abstract

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