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Fluorous mixture synthesis: A fluorous-tagging strategy for the synthesis and separation of mixtures of organic compounds

Luo, Z and Zhang, Q and Oderaotoshi, Y and Curran, DP (2001) Fluorous mixture synthesis: A fluorous-tagging strategy for the synthesis and separation of mixtures of organic compounds. Science, 291 (5509). 1766 - 1769. ISSN 0036-8075

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Abstract

The solution-phase synthesis of organic compounds as mixtures rather than in individual pure form offers efficiency advantages that are negated by the difficulty in separating and identifying the components of the final mixture. Here, a strategy for mixture synthesis that addresses these separation and identification problems is presented. A series of organic substrates was tagged with a series of fluorous tags of increasing fluorine content. The compounds were then mixed, and multistep reactions were conducted to make enantiomers or analogs of the natural product mappicine. The resulting tagged products were then demixed by fluorous chromatography (eluting in order of increasing fluorine content) to provide the individual pure components of the mixture, which were detagged to release the final products.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Luo, Z
Zhang, Q
Oderaotoshi, Y
Curran, DPcurran@pitt.eduCURRAN
Date: 2 March 2001
Date Type: Publication
Journal or Publication Title: Science
Volume: 291
Number: 5509
Page Range: 1766 - 1769
DOI or Unique Handle: 10.1126/science.1057567
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0036-8075
MeSH Headings: Alkaloids--chemical synthesis; Alkaloids--chemistry; Chromatography; Chromatography, Gel--methods; Combinatorial Chemistry Techniques; Fluorine--analysis; Organic Chemicals--chemical synthesis; Organic Chemicals--isolation & purification; Spectrum Analysis; Stereoisomerism
PubMed ID: 11230688
Date Deposited: 14 Feb 2014 16:50
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/20550

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