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Quasiracemic synthesis: Concepts and implementation with a fluorous tagging strategy to make both enantiomers of pyridovericin and mappicine

Zhang, Q and Rivkin, A and Curran, DP (2002) Quasiracemic synthesis: Concepts and implementation with a fluorous tagging strategy to make both enantiomers of pyridovericin and mappicine. Journal of the American Chemical Society, 124 (20). 5774 - 5781. ISSN 0002-7863

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Abstract

The concept of quasiracemic synthesis is introduced and illustrated with syntheses of both enantiomers of pyridovericin (whose absolute configuration is assigned as R) and mappicine. Like racemic synthesis, quasiracemic synthesis provides both enantiomers in a single synthetic sequence; however, separation tagging is used to ensure that quasiracemic mixtures can be analyzed, separated, and identified on demand. Fluorous tags of differing chain lengths are used to tag two enantiomeric starting materials. The resulting quasienantiomers are mixed to make a quasiracemate, which is then treated like a true racemate in successive steps of the synthesis. Fluorous chromatography is used to separate, or demix, the final quasiracemate into its two components, which are then detagged to provide (true) enantiomeric products. Quasiracemic synthesis is portrayed as the first and simplest of a series of mixture synthesis techniques based on separation tagging, and the prospects for using other types of separation tags are briefly evaluated.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Zhang, Q
Rivkin, A
Curran, DPcurran@pitt.eduCURRAN
Date: 22 May 2002
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 124
Number: 20
Page Range: 5774 - 5781
DOI or Unique Handle: 10.1021/ja025606x
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Alkaloids--chemical synthesis; Alkaloids--chemistry; Anti-Bacterial Agents--chemical synthesis; Anti-Bacterial Agents--chemistry; Hydrocarbons, Fluorinated--chemistry; Nuclear Magnetic Resonance, Biomolecular--methods; Pyridones--chemical synthesis; Pyridones--chemistry; Stereoisomerism
PubMed ID: 12010052
Date Deposited: 13 Feb 2014 16:31
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/20504

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