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Fluorous mixture synthesis of fused-tricyclic hydantoins. Use of a redundant tagging strategy on fluorinated substrates

Manku, S and Curran, DP (2005) Fluorous mixture synthesis of fused-tricyclic hydantoins. Use of a redundant tagging strategy on fluorinated substrates. Journal of Organic Chemistry, 70 (11). 4470 - 4473. ISSN 0022-3263

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Abstract

Simple HPLC experiments were used to identify a redundant tagging scheme wherein six different amino acids were tagged with only four fluorous tags. The tagged amino acids were converted to regiosiomeric mixtures of tricyclic hydantoins. Despite the lack of selectivity, the mixtures were demixed and detagged to give 11 individual pure products in just 25 steps. © 2005 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Manku, S
Curran, DPcurran@pitt.eduCURRAN
Date: 27 May 2005
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 70
Number: 11
Page Range: 4470 - 4473
DOI or Unique Handle: 10.1021/jo0502596
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Amino Acids--chemistry; Chemistry, Organic--methods; Chromatography, High Pressure Liquid; Hydantoins--chemical synthesis; Hydantoins--chemistry; Hydrocarbons, Fluorinated--chemical synthesis; Hydrocarbons, Fluorinated--chemistry; Molecular Structure
PubMed ID: 15903326
Date Deposited: 03 Jul 2013 14:26
Last Modified: 02 Feb 2019 15:59
URI: http://d-scholarship.pitt.edu/id/eprint/19214

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