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

Baoyu Xue, Junhong Zhao, Yange Fan, Shipeng Chen, Wenfeng Li, Jin Chen, Zheng Li, Hongxing Wang, Hongjun Kong

2020Chemistry & Biodiversity18 citationsDOI

Abstract

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.

Topics & Concepts

DocetaxelChemistryPaclitaxelStereochemistryPharmacologyCombinatorial chemistryInternal medicineChemotherapyMedicineCancer Treatment and PharmacologySynthetic Organic Chemistry MethodsMicrobial Natural Products and Biosynthesis