Studies on Iejimalide B: Preparation of the Seco Acid and Identification of the Molecule's “Achilles Heel”†
Alois Fürstner Prof.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorChristophe Aïssa Dr.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorCarine Chevrier Dr.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorFilip Teplý Dr.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorCristina Nevado Dr.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorMartin Tremblay Dr.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorAlois Fürstner Prof.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorChristophe Aïssa Dr.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorCarine Chevrier Dr.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorFilip Teplý Dr.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorCristina Nevado Dr.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorMartin Tremblay Dr.
Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany, Fax: (+49) 208-306-2994
Search for more papers by this authorGenerous financial support from the MPG, the Fonds der Chemischen Industrie, the Alexander-von-Humboldt Foundation (fellowship to C.N.), and the NSERC, Canada (fellowship to M.T.) is gratefully acknowledged. We thank Dr. R. Riveiros for assistance in the initial phase of this project, and Dr. R. Mynott, B. Gabor, and C. Wirtz for their invaluable help with the structure assignment of several key compounds.
Graphical 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.
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2006/z601859_s.pdf or from the author.
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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