[C+NC+CC] Coupling-Enabled Synthesis of Influenza Neuramidase Inhibitor A-315675

An efficient synthesis of the neuramidase inhibitor A-315675 is reported. The fully functionalized pyrrolidine core of the target is assembled in one pot via an exo-selective asymmetric [C+NC+CC] coupling reaction.

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 5; pp. 1326 - 1329
Main Authors Garner, Philip, Weerasinghe, Laksiri, Youngs, Wiley J, Wright, Brian, Wilson, Dean, Jacobs, Dylan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.03.2012
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Enzyme Inhibitors - chemical synthesis
Models, Molecular
Molecular Structure
Neuraminidase - antagonists & inhibitors
Orthomyxoviridae - enzymology
Physical Sciences
Pyrrolidines - chemical synthesis
Science & Technology
Stereoisomerism
RESISTANT
NEURAMINIDASE INHIBITOR
CYANOCYCLINE
VIRUSES
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Abstract An efficient synthesis of the neuramidase inhibitor A-315675 is reported. The fully functionalized pyrrolidine core of the target is assembled in one pot via an exo-selective asymmetric [C+NC+CC] coupling reaction.
AbstractList An efficient synthesis of the neuramidase inhibitor A-315675 is reported. The fully functionalized pyrrolidine core of the target is assembled in one pot via an exo-selective asymmetric [C+NC+CC] coupling reaction.
Author Youngs, Wiley J
Jacobs, Dylan
Wright, Brian
Wilson, Dean
Garner, Philip
Weerasinghe, Laksiri
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  givenname: Wiley J
  surname: Youngs
  fullname: Youngs, Wiley J
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  fullname: Wilson, Dean
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  surname: Jacobs
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/22339284$$D View this record in MEDLINE/PubMed
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Cites_doi 10.1128/AAC.01276-08
10.1016/j.bmcl.2008.01.048
10.1021/ol017268v
10.1016/S0957-4166(03)00597-4
10.1128/AAC.49.11.4515-4520.2005
10.1093/infdis/jiq010
10.1021/jo200553g
10.1016/j.tetlet.2007.12.080
10.1016/j.antiviral.2007.08.008
10.1021/ol061113b
10.1021/jo800879e
10.1021/jo0162890
10.1055/s-0028-1088021
10.1021/jm049276y
10.1016/j.tetlet.2007.03.145
10.1021/ja077853c
10.1021/ja0126226
10.1128/JVI.76.11.5380-5386.2002
10.2174/157017910791414517
10.1055/s-2002-31969
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NEURAMINIDASE INHIBITOR
CYANOCYCLINE
VIRUSES
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Snippet An efficient synthesis of the neuramidase inhibitor A-315675 is reported. The fully functionalized pyrrolidine core of the target is assembled in one pot via...
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SubjectTerms Chemistry
Chemistry, Organic
Enzyme Inhibitors - chemical synthesis
Models, Molecular
Molecular Structure
Neuraminidase - antagonists & inhibitors
Orthomyxoviridae - enzymology
Physical Sciences
Pyrrolidines - chemical synthesis
Science & Technology
Stereoisomerism
Title [C+NC+CC] Coupling-Enabled Synthesis of Influenza Neuramidase Inhibitor A-315675
URI http://dx.doi.org/10.1021/ol3002128
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https://www.ncbi.nlm.nih.gov/pubmed/22339284
https://search.proquest.com/docview/926155426
Volume 14
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