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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Abstract

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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Details

Item Type:	Article
Status:	Published
Creators/Authors:	Creators Email Pitt Username ORCID Frantz, MC Pierce, JG Pierce, JM Kangying, L Qingwei, W Johnson, M Wipf, P pwipf@pitt.edu PWIPF
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
URI:	http://d-scholarship.pitt.edu/id/eprint/18744

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