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Journal Article

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

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons58380

Fürstner,  A.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58387

Aïssa,  C.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58487

Chevrier,  C.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons59040

Teplý,  F.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58845

Nevado,  C.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons59055

Tremblay,  M.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Supplementary Material (public)

z601859_s.pdf
(Supplementary material), 73KB

Citation

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.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0025-AD46-8
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.