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  Total Synthesis and Biological Evaluation of the Cytotoxic Resin Glycosides Ipomoeassin A-F and Analogues

Nagano, T., Pospíšil, J., Chollet, G., Schulthoff, S., Hickmann, V., Moulin, E., et al. (2009). Total Synthesis and Biological Evaluation of the Cytotoxic Resin Glycosides Ipomoeassin A-F and Analogues. Chemistry – A European Journal, 15(38), 9697-9706. doi:10.1002/chem.200901449.

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[266]SI.pdf (Supplementary material), 278KB
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[266]SI.pdf
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Supporting Information
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2009
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Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
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 Creators:
Nagano, Takashi1, Author              
Pospíšil, Jiří1, Author              
Chollet, Guillaume1, Author              
Schulthoff, Saskia1, Author              
Hickmann, Volker1, Author              
Moulin, Emilie1, Author              
Herrmann, Jennifer2, Author
Müller, Rolf2, Author
Fürstner, Alois1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Saarland University, Department of Pharmaceutical Biotechnology, 66041 Saarbrücken (Germany), ou_persistent22              

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Free keywords: cytotoxicity; glycolipids; macrocycles; metathesis; protecting groups
 Abstract: A multitasking C-silylation strategy using the readily available compound 26 as a surrogate for cinnamic acid represents the key design element of a total synthesis of all known members of the ipomoeassin family of resin glyosides. This protecting group maneuver allows the unsaturated acids decorating the glucose subunit of the targets to be attached at an early phase of the synthesis, prevents their participation in the ruthenium-catalyzed ring-closing metathesis (RCM) used to form the macrocyclic ring, and protects them against reduction during the hydrogenation of the resulting cycloalkene over Wilkinson’s catalyst. As the C-silyl group can be concomitantly removed with the O-TBS substituent using tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) in acetonitrile, no separate protecting group manipulations were necessary in the final stages, thus contributing to a favorable overall “economy of steps”. In addition to the naturally occurring ipomoeassins, a small set of synthetic analogues has also been prepared by “diverted total synthesis”. The cytotoxicity of these compounds was assayed with two different cancer cell lines. The recorded data confirm previous findings that the acylation- and oxygenation pattern of these amphiphilic glycoconjugates is highly correlated with their biological activity profile. Ipomoeassin F turned out to be the most promising member of the series, showing IC50 values in the low nanomolar range.

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Language(s): eng - English
 Dates: 2009-05-292009-08-202009-09-28
 Publication Status: Published in print
 Pages: 10
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: eDoc: 473967
DOI: 10.1002/chem.200901449
ISI: 000270435600014
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: - Volume / Issue: 15 (38) Sequence Number: - Start / End Page: 9697 - 9706 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058