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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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z601859_s.pdf (Supplementary material), 73KB
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z601859_s.pdf
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Copyright Date:
2006
Copyright Info:
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: Published in print
 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