The Development of a Practical Total Synthesis of Discodermolide, a Promising Microtubule-Stabilizing Anticancer Agent

Ian Paterson, Gordon John Florence

Research output: Contribution to journalArticlepeer-review

99 Citations (Scopus)

Abstract

Marine organisms provide an important source of natural product diversity with an associated range of significant biological activities. Discodermolide, isolated in microscopic quantities from a deep-water sponge, shares the same microtubule-stabilizing mechanism as Taxol and has a promising antitumor profile. There is, however, a chronic supply problem hampering clinical development and so a practical total synthesis of discodermolide is an important goal. This review highlights the completed total syntheses of discodermolide, focusing on the various methods and strategies employed for achieving stereocontrol and realising the pivotal fragment couplings. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

Original languageEnglish
Pages (from-to)2193-2208
Number of pages16
JournalEuropean Journal of Organic Chemistry
Volume2003
Issue number12
DOIs
Publication statusPublished - Jun 2003

Keywords

  • antitumor agents
  • cytotoxic
  • marine polyketides
  • total synthesis
  • tubulin
  • LACTATE-DERIVED KETONES
  • MARINE NATURAL-PRODUCTS
  • PI-FACE SELECTIVITY
  • MEDIATED ALDOL REACTIONS
  • GRAM-SCALE SYNTHESIS
  • MEDIUM RING ETHERS
  • STEREOSELECTIVE SYNTHESIS
  • POLYPROPIONATE SYNTHESIS
  • STEREOCONTROLLED SYNTHESIS
  • ASYMMETRIC-SYNTHESIS

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