Synthesis of Taxol and Docetaxel by Using 10-Deacetyl-7-xylosyltaxanes
- PMID: 31967396
- DOI: 10.1002/cbdv.201900631
Synthesis of Taxol and Docetaxel by Using 10-Deacetyl-7-xylosyltaxanes
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.
© 2020 Wiley-VHCA AG, Zurich, Switzerland.
References
-
- M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon, A. T. McPhail, ‘Plant antitumor agents. VI. The isolation and structure of Taxol, a novel antileukemic and antitumor agent from Taxus brevifolia’, J. Am. Chem. Soc. 1971, 93, 2325-2327.
-
- M. E. Wall, M. C. Wani, ‘Camptothecin and Taxol: discovery to clinic thirteenth Bruce F. Cain Memorial Award Lecture’, Cancer Res. 1995, 55, 753-760.
-
- E. K. Rowinsky, R. C. Donehower, N. B. Rosenshein, D. S. Ettinger, W. P. McGuire, ‘Phase II study of Taxol in advanced ovarian epithelial malignancies’, Proc. Am. Soc. Clin. Oncol. 1988, 136.
-
- D. Z. Chen, L Wu, D. M. Chen, ‘Cultivation and utilization of imported tree species’, Yunnan Sci. Technol. Press, 2010, pp. 111-117.
-
- Y. Li, ‘Design, Synthesis and Evaluation of Novel Taxane-Based Anticancer Agents’, State University of New York at Stony Brook, 2011.
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