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Synfacts 2007(7): 0681-0681  
DOI: 10.1055/s-2007-968609
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Discodermolide

Contributor(s): Philip Kocienski, Thomas Snaddon
E. de Lemos, F.-H. Porée, A. Commerçon, J.-F. Betzer, A. Pancrazi, J. Ardisson*
Université de Cergy-Pointoise and Sanofi-Aventis, Vitry-sur-Seine, France
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Publication History

Publication Date:
22 June 2007 (online)

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Significance

Discodermolide is a marine polyketide that displays pronounced anticancer activity. It is an antimitotic agent that acts by stabilizing microtubules. In this synthesis, the Hoppe crotyltitanation reaction (D. Hoppe, O. Zschage Angew. Chem. Int. Ed. 1989, 28, 69-71) plays a key strategic role to install the syn-anti methyl-hydroxy-methyl stereotriads prevalent throughout the structure.