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Fluorous Mixture Synthesis of Stereoisomer Libraries: Total Syntheses of (+)-Murisolin and Fifteen Diastereoisomers

Zhang, Q and Lu, H and Richard, C and Curran, DP (2004) Fluorous Mixture Synthesis of Stereoisomer Libraries: Total Syntheses of (+)-Murisolin and Fifteen Diastereoisomers. Journal of the American Chemical Society, 126 (1). 36 - 37. ISSN 0002-7863

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Abstract

The synthesis of a stereoisomer library of 16 murisolins in individual pure form by fluorous mixture synthesis is reported. Four stereoisomeric precursors are tagged with different fluorous tags, and the resulting mixture is taken through the synthesis with four splits and late stage demixing and detagging to give all 16 products. These products exhibit only six different sets of NMR spectra, but all can be differentiated by chiral HPLC. The structure of murisolin is confirmed, but the structures of murisolin A and 16,19-cis-murisolin may never be known with certainty because insufficient data were collected on natural samples to differentiate each of them from one other isomer. Copyright © 2004 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Zhang, Q
Lu, H
Richard, C
Curran, DPcurran@pitt.eduCURRAN
Date: 14 January 2004
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 126
Number: 1
Page Range: 36 - 37
DOI or Unique Handle: 10.1021/ja038542e
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Furans--chemical synthesis; Furans--chemistry; Stereoisomerism
PubMed ID: 14709047
Date Deposited: 30 Oct 2013 16:59
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/19920

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