Synthesis of 4-deacetyl-1-dimethylsilyl-7-triethylsilylbaccatin III

J Org Chem. 2009 Mar 6;74(5):2186-8. doi: 10.1021/jo802598m.

Abstract

A one-pot trisilylation step to protect three hydroxyl groups of baccatin III (1), followed by hydride ester cleavage and base hydrolysis of a triethylsilyl ether at C13, provides efficient access to a key intermediate 9 (top path). This route removes two steps from a previously established reaction sequence to 9 (bottom path). In principle, inclusion of the truncated reaction sequence into widely utilized semisynthetic routes to next generation Taxol (paclitaxel) compounds could conceivably shorten the overall process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry*
  • Molecular Conformation
  • Stereoisomerism
  • Taxoids / chemical synthesis*
  • Taxoids / chemistry*
  • Trimethylsilyl Compounds / chemical synthesis*
  • Trimethylsilyl Compounds / chemistry

Substances

  • 4-deacetyl-1-dimethylsilyl-7-triethylsilylbaccatin III
  • Alkaloids
  • Taxoids
  • Trimethylsilyl Compounds
  • baccatin III