Chapter 2. Chemical Synthesis and Biological Studies of the Epothilones - Microtubule Stabilizing Agents with Enhanced Activity Against Multidrug-Resistant Cell Lines and Tumors.

  1. Ehud Keinan and
  2. Israel Schechter
  1. Christina R. Harris,
  2. Scott D. Kuduk and
  3. Samuel J. Danishejky

Published Online: 14 DEC 2007

DOI: 10.1002/9783527612949.ch02

Chemistry for the 21st Century

Chemistry for the 21st Century

How to Cite

Harris, C. R., Kuduk, S. D. and Danishejky, S. J. (2000) Chemical Synthesis and Biological Studies of the Epothilones - Microtubule Stabilizing Agents with Enhanced Activity Against Multidrug-Resistant Cell Lines and Tumors., in Chemistry for the 21st Century (eds E. Keinan and I. Schechter), Wiley-VCH Verlag GmbH, Weinheim, Germany. doi: 10.1002/9783527612949.ch02

Editor Information

  1. Department of Chemistry Technion - Israel Institute of Technology, Haifa 32000, Israel

Publication History

  1. Published Online: 14 DEC 2007
  2. Published Print: 20 DEC 2000

ISBN Information

Print ISBN: 9783527302352

Online ISBN: 9783527612949

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Keywords:

  • epothilones;
  • epothilone synthesis;
  • B-Alkyl Suzuki strategy;
  • macrolactonization;
  • stereoselective Noyori reduction

Summary

This chapter contains sections titled:

  • Introduction

  • Total Synthesis of Epothilones

  • First Generation Syntheses of Epothilones A and B

  • First Generation Synthesis of the Acyl Domain

  • Investigation of C9–C10 Bond Construction Through Ring Closing Metathesis.

  • B-Alkyl Suzuki Strategy

  • Macrolactonization and Macroaldolization Approaches

  • A New and More Efficient Synthesis of Epothilone B

  • Dianion Equivalents Corresponding to the Polypropionate Domain of Epothilone B

  • B-Alkyl Suzuki Merger

  • Stereoselective Noyori Reduction

  • Discovery of a Remarkable Long-Range Effkct on the Double Diastereoface Selectivity in an Aldol Condensation

  • Preparation of Other Epothilone Analogs

  • Biological Evaluation of Epothilones

  • SAR Analysis of Epothilones: The Zone Approach

  • In Vitro Analysis Comparison to Paclitaxel and Related Agents

  • In Vivo Analysis: Comparisons to Paditaxel

  • Conclusions

  • Acknowledgements