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

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‐butylox...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2006-09, Vol.45 (35), p.5832-5837
Main Authors: Fürstner, Alois, Aïssa, Christophe, Chevrier, Carine, Teplý, Filip, Nevado, Cristina, Tremblay, Martin
Format: Article
Language:English
Subjects:
Heck reaction
lactones
macrolides
olefination
total synthesis
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200601859