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Confirmation of the stereostructure of (+)-cytostatin by fluorous mixture synthesis of four candidate stereoisomers

Jung, WH and Guyenne, S and Riesco-Fagundo, C and Mancuso, J and Nakamura, S and Curran, DP (2008) Confirmation of the stereostructure of (+)-cytostatin by fluorous mixture synthesis of four candidate stereoisomers. Angewandte Chemie - International Edition, 47 (6). 1130 - 1133. ISSN 1433-7851

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Abstract

Mix and match: Four closely related candidate isomers for cytostatin have been synthesized by using the technique of fluorous mixture synthesis. Comparison of NMR, thin-layer chromatography, and optical rotation data enabled the three isomers that were not cytostatin to be identified. Thus, by a process of elimination (disproof), the isomer corresponding to cytostatin was determined, and the 4S,5S,6S,9S,10S,11S configuration confirmed. (Chemical Equation Presented). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Jung, WH
Guyenne, S
Riesco-Fagundo, C
Mancuso, J
Nakamura, S
Curran, DPcurran@pitt.eduCURRAN
Date: 11 February 2008
Date Type: Publication
Journal or Publication Title: Angewandte Chemie - International Edition
Volume: 47
Number: 6
Page Range: 1130 - 1133
DOI or Unique Handle: 10.1002/anie.200704893
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1433-7851
MeSH Headings: Fluorine Compounds--chemistry; Molecular Structure; Organophosphates--chemical synthesis; Organophosphates--chemistry; Pyrones--chemical synthesis; Pyrones--chemistry; Stereoisomerism
PubMed ID: 18175302
Date Deposited: 08 Apr 2013 17:20
Last Modified: 02 Feb 2019 15:59
URI: http://d-scholarship.pitt.edu/id/eprint/18101

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