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  Studies on Iejimalide B: Preparation of the Seco Acid and Identification of the Molecule's "Achilles Heel"

Fürstner, A., Aïssa, C., Chevrier, C., Teplý, F., Nevado, C., & Tremblay, M. (2006). Studies on Iejimalide B: Preparation of the Seco Acid and Identification of the Molecule's "Achilles Heel". Angewandte Chemie International Edition, 45(35), 5832-5837. doi:10.1002/anie.200601859.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0025-AD46-8 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0025-AD47-6
Genre: Journal Article

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z601859_s.pdf (Supplementary material), 73KB
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https://hdl.handle.net/11858/00-001M-0000-0025-AD48-4
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z601859_s.pdf
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Copyright Date:
2006
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Wiley-VCH, 69451 Weinheim, Germany
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 Creators:
Fürstner, A.1, Author           
Aïssa, C.1, Author           
Chevrier, C.1, Author           
Teplý, F.1, Author           
Nevado, C.1, Author           
Tremblay, M.1, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Free keywords: Heck reaction; lactones; macrolides; olefination; total synthesis
 Abstract: Limitations of models in total synthesis are illustrated by a study towards the potent cytotoxic macrolide iejimalide B. Although the Yamaguchi protocol allowed for the esterification of elaborate segments, attempted macrolactonization of the seco acid met with failure (see scheme, Boc= tert-butyloxycarbonyl). The assembly of the seco acid involves some of the most advanced applications of the Julia olefination known to date.

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Language(s): eng - English
 Dates: 2006-05-112006-05-042006-09-04
 Publication Status: Issued
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.200601859
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH Verlag GmbH & Co. KGaA
Pages: - Volume / Issue: 45 (35) Sequence Number: - Start / End Page: 5832 - 5837 Identifier: ISSN: 1521-3773
CoNE: https://pure.mpg.de/cone/journals/resource/0570-0833