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Large-scale asymmetric synthesis of the bioprotective agent JP4-039 and analogs

Frantz, MC and Pierce, JG and Pierce, JM and Kangying, L and Qingwei, W and Johnson, M and Wipf, P (2011) Large-scale asymmetric synthesis of the bioprotective agent JP4-039 and analogs. Organic Letters, 13 (9). 2318 - 2321. ISSN 1523-7060

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Chemical equations presented. JP4-039 is a novel nitroxide conjugate capable of crossing lipid bilayer membranes and scavenging reactive oxygen species (ROS). An efficient and scalable one-pot hydrozirconation- transmetalation-imine addition methodology has been developed for its asymmetric preparation. Furthermore, this versatile methodology allows for the synthesis of cyclopropyl and fluorinated analogs of the parent lead structure. © 2011 American Chemical Society.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Frantz, MC
Pierce, JG
Pierce, JM
Kangying, L
Qingwei, W
Johnson, M
Wipf, Ppwipf@pitt.eduPWIPF
Date: 6 May 2011
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 13
Number: 9
Page Range: 2318 - 2321
DOI or Unique Handle: 10.1021/ol200567p
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Amines--chemistry; Esters--chemistry; Models, Molecular; Molecular Structure; Nitrogen Oxides--chemical synthesis; Stereoisomerism
Other ID: NLM NIHMS285383, NLM PMC3089766
PubMed Central ID: PMC3089766
PubMed ID: 21452836
Date Deposited: 28 May 2013 15:23
Last Modified: 02 Feb 2019 15:57


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