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Fluorous mixture synthesis of (-)-dictyostatin and three stereoisomers

Fukui, Y and Bruckner, AM and Shin, Y and Balachandran, R and Day, BW and Curran, DP (2006) Fluorous mixture synthesis of (-)-dictyostatin and three stereoisomers. Organic Letters, 8 (2). 301 - 304. ISSN 1523-7060

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Abstract

A mixture of four stereoisomers whose configurations are encoded by fluorous silyl protecting groups has been prepared and converted over 22 steps to a mixture of protected dictyostatins. Demixing by fluorous HPLC followed by removal of the fluorous protecting groups (detagging) provides dictyostatin and three C6,C7 stereoisomers. Biological evaluation showed that the monoepimers of the natural product retained highly potent activity. © 2006 American Chemical Society.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Fukui, Y
Bruckner, AM
Shin, Y
Balachandran, R
Day, BW
Curran, DPcurran@pitt.eduCURRAN
Date: 19 January 2006
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 8
Number: 2
Page Range: 301 - 304
DOI or Unique Handle: 10.1021/ol0526827
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Fluorine--chemistry; Macrolides--chemical synthesis; Macrolides--chemistry; Molecular Structure; Stereoisomerism
PubMed ID: 16408900
Date Deposited: 17 Jun 2013 16:04
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship-dev.library.pitt.edu/id/eprint/19022

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