Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated stille coupling

Mark S. Jensen; Chunhua Yang; Yi Hsiao; Nelo Rivera; Kenneth M. Wells; John Y.L. Chung; Nobuyoshi Yasuda; David L. Hughes; Paul J. Reider

doi:10.1021/ol005641d

Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated stille coupling

Mark S. Jensen
, Chunhua Yang
, Yi Hsiao
, Nelo Rivera
, Kenneth M. Wells
, John Y.L. Chung
, Nobuyoshi Yasuda
, David L. Hughes
, Paul J. Reider

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

85 Scopus citations

Abstract

A short synthesis of carbapenem 1 is described. The key step involves the cross-coupling of an enol triflate with an amino-substituted sp³ carbon. This cross-couping, which allows the introduction of the complete side chain in one step, utilizes a stannatrane as the heteroalkyl transfer reagent.

Original language	English (US)
Pages (from-to)	1081-1083
Number of pages	3
Journal	Organic letters
Volume	2
Issue number	8
DOIs	https://doi.org/10.1021/ol005641d
State	Published - Apr 20 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol005641d

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title = "Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated stille coupling",

abstract = "A short synthesis of carbapenem 1 is described. The key step involves the cross-coupling of an enol triflate with an amino-substituted sp3 carbon. This cross-couping, which allows the introduction of the complete side chain in one step, utilizes a stannatrane as the heteroalkyl transfer reagent.",

author = "Jensen, \{Mark S.\} and Chunhua Yang and Yi Hsiao and Nelo Rivera and Wells, \{Kenneth M.\} and Chung, \{John Y.L.\} and Nobuyoshi Yasuda and Hughes, \{David L.\} and Reider, \{Paul J.\}",

year = "2000",

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doi = "10.1021/ol005641d",

language = "English (US)",

volume = "2",

pages = "1081--1083",

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T1 - Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated stille coupling

AU - Jensen, Mark S.

AU - Yang, Chunhua

AU - Hsiao, Yi

AU - Rivera, Nelo

AU - Wells, Kenneth M.

AU - Chung, John Y.L.

AU - Yasuda, Nobuyoshi

AU - Hughes, David L.

AU - Reider, Paul J.

PY - 2000/4/20

Y1 - 2000/4/20

N2 - A short synthesis of carbapenem 1 is described. The key step involves the cross-coupling of an enol triflate with an amino-substituted sp3 carbon. This cross-couping, which allows the introduction of the complete side chain in one step, utilizes a stannatrane as the heteroalkyl transfer reagent.

AB - A short synthesis of carbapenem 1 is described. The key step involves the cross-coupling of an enol triflate with an amino-substituted sp3 carbon. This cross-couping, which allows the introduction of the complete side chain in one step, utilizes a stannatrane as the heteroalkyl transfer reagent.

UR - https://www.scopus.com/pages/publications/0034689877

UR - https://www.scopus.com/pages/publications/0034689877#tab=citedBy

U2 - 10.1021/ol005641d

DO - 10.1021/ol005641d

M3 - Article

C2 - 10804559

AN - SCOPUS:0034689877

SN - 1523-7060

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JO - Organic letters

JF - Organic letters

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ER -

Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated stille coupling

Abstract

All Science Journal Classification (ASJC) codes

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