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The Chemical Synthesis of Discodermolide

  • I. Paterson
  • G. J. Florence
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 286)

Abstract

The marine sponge-derived polyketide discodermolide is a potent antimitotic agent that represents a promising natural product lead structure in the treatment of cancer. Discodermolide shares the same microtubule-stabilising mechanism of action as Taxol®, inhibits the growth of solid tumours in animal models and shows synergy with Taxol. The pronounced cytotoxicity of discodermolide, which is maintained against cancer cell lines that display resistance to Taxol and other drugs, combined with its scarce availability from its natural source, has fuelled significant academic and industrial interest in devising a practical total synthesis as a means of ensuring a sustainable supply for drug development. This chapter surveys the various total syntheses of discodermolide that have been completed over the period 1993–2007, focusing on the strategies employed for introduction of the multiple stereocentres and achieving control over the alkene geometry, along with the various methods used for realising the pivotal fragment couplings to assemble progressively the full carbon skeleton. This dedicated synthetic effort has triumphed in removing the supply problem for discodermolide, providing sufficient material for extensive biological studies and enabling its early stage clinical development, as well as facilitating SAR studies for lead optimisation.

Keywords

Anticancer Natural products Polyketides Stereocontrol Tubulin 

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© Springer-Verlag Berlin Heidelberg 2008

Authors and Affiliations

  1. 1.University Chemical LaboratoryCambridge CB2 1EWUK
  2. 2.School of Chemistry and Centre for Biomolecular Sciences University of St AndrewsNorth HaughUK

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