Synthesis of Taxol and Docetaxel by Using 10-Deacetyl-7-xylosyltaxanes

Chem Biodivers. 2020 Feb;17(2):e1900631. doi: 10.1002/cbdv.201900631. Epub 2020 Jan 22.

Abstract

A mixture of taxols was prepared from 10-deacetyl-7-xylosyltaxanes by three-step reactions: redox, acetylation, and deacetylation. The mixture was separated by column chromatography on silica gel to afford Taxol, Taxol B (Cephalomannine) and Taxol C. The mixture of Taxol B and Taxol C was converted to Docetaxel by Schwartz's reagent. The structures of Taxol and Docetaxel were characterized by HPLC, 1 H-NMR, 13 C-NMR and MS. This synthetic process has expanded the source of biomass for the chemical semi-synthesis of Taxol and Docetaxel, reduced the production costs, and increased the biomass resource of taxanes.

Keywords: Docetaxel; Taxol; synthesis; taxane compounds.

MeSH terms

  • Acetylation
  • Chromatography, High Pressure Liquid
  • Docetaxel / chemical synthesis
  • Docetaxel / chemistry*
  • Magnetic Resonance Spectroscopy
  • Oxidation-Reduction
  • Paclitaxel / chemical synthesis
  • Paclitaxel / chemistry*
  • Taxoids / chemistry*

Substances

  • Taxoids
  • Docetaxel
  • Paclitaxel