N-methylation of the c3' amide of taxanes: synthesis of N-methyltaxol C and N-methylpaclitaxel

J Org Chem. 2008 Jun 20;73(12):4705-8. doi: 10.1021/jo800173h. Epub 2008 May 23.

Abstract

A method has been developed for the methylation of the C3' amide of taxol C and paclitaxel. Taxol C and paclitaxel were sequentially silylated at the 2', 7, and 1-hydroxyl groups with tert-butyldimethylsilyl chloride, triethylsilyl chloride, and dimethylsilyl chloride, respectively. Subsequent reaction with potassium tert-butoxide and methyl iodide provided the corresponding N-methylated taxane derivatives. Removal of the silyl protecting groups furnished N-methyltaxol C and N-methylpaclitaxel.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Magnetic Resonance Spectroscopy
  • Methylation
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Infrared
  • Taxoids / chemical synthesis
  • Taxoids / chemistry*

Substances

  • Amides
  • Taxoids