Synthesis of a functionalized oxabicyclo[2.2.1]-heptene-based chemical library

Sarah B. Luesse; Gregg Wells; Jeanne Miller; Erin Bolstad; Stephen C. Bergmeier; Mark C. McMills; Nigel D. Priestley; Dennis L. Wright

doi:10.2174/138620712798280835

Synthesis of a functionalized oxabicyclo[2.2.1]-heptene-based chemical library

Sarah B. Luesse, Gregg Wells, Jeanne Miller, Erin Bolstad, Stephen C. Bergmeier, Mark C. McMills, Nigel D. Priestley, Dennis L. Wright

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

4 Scopus citations

Abstract

The 7-oxabicyclo[2.2.1]heptene ring system is a common structural motif in many pharmacologically interesting molecules. We recognized the potential to employ this highly oxygenated and conformationally-restricted scaffold in diversity-oriented synthesis to generate a library of non-chiral but topologically complex compounds. Herein, we report the synthesis and biological evaluation of two 96-member tricyclic libraries containing the oxabicyclo[2.2.1]heptene framework using acetal formation as the key step.

Original language	English
Pages (from-to)	81-89
Number of pages	9
Journal	Combinatorial Chemistry and High Throughput Screening
Volume	15
Issue number	1
DOIs	https://doi.org/10.2174/138620712798280835
State	Published - Jan 2012

Keywords

Acetal
Antibacterial
Oxabicyclo[2.2.1]heptene

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abstract = "The 7-oxabicyclo[2.2.1]heptene ring system is a common structural motif in many pharmacologically interesting molecules. We recognized the potential to employ this highly oxygenated and conformationally-restricted scaffold in diversity-oriented synthesis to generate a library of non-chiral but topologically complex compounds. Herein, we report the synthesis and biological evaluation of two 96-member tricyclic libraries containing the oxabicyclo[2.2.1]heptene framework using acetal formation as the key step.",

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AU - Luesse, Sarah B.

AU - Wells, Gregg

AU - Miller, Jeanne

AU - Bolstad, Erin

AU - Bergmeier, Stephen C.

AU - McMills, Mark C.

AU - Priestley, Nigel D.

AU - Wright, Dennis L.

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AB - The 7-oxabicyclo[2.2.1]heptene ring system is a common structural motif in many pharmacologically interesting molecules. We recognized the potential to employ this highly oxygenated and conformationally-restricted scaffold in diversity-oriented synthesis to generate a library of non-chiral but topologically complex compounds. Herein, we report the synthesis and biological evaluation of two 96-member tricyclic libraries containing the oxabicyclo[2.2.1]heptene framework using acetal formation as the key step.

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KW - Antibacterial

KW - Oxabicyclo[2.2.1]heptene

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JF - Combinatorial Chemistry and High Throughput Screening

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Synthesis of a functionalized oxabicyclo[2.2.1]-heptene-based chemical library

Abstract

Keywords

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