Semisynthesis of D-ring modified taxoids: novel thia derivatives of docetaxel

L Mercklé; J Dubois; E Place; S Thoret; F Guéritte; D Guénard; C Poupat; A Ahond; P Potier

doi:10.1021/jo015539+

Semisynthesis of D-ring modified taxoids: novel thia derivatives of docetaxel

J Org Chem. 2001 Jul 27;66(15):5058-65. doi: 10.1021/jo015539+.

Authors

L Mercklé¹, J Dubois, E Place, S Thoret, F Guéritte, D Guénard, C Poupat, A Ahond, P Potier

Affiliation

¹ Institut de Chimie des Substances Naturelles, CNRS 91198 Gif sur Yvette Cedex, France.

PMID: 11463257
DOI: 10.1021/jo015539+

Abstract

Two novel 5(20)-thia analogues of docetaxel have been synthesized from 10-deacetylbaccatin III or taxine B and isotaxine B. The key step of these syntheses is the concomitant thietane ring formation and acetylation of the tertiary alcohol at C-4. Both compounds are less cytotoxic than docetaxel but have divergent activity on microtubule disassembly.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / chemical synthesis*
Antineoplastic Agents, Phytogenic / pharmacology
Docetaxel
Humans
Indicators and Reagents
KB Cells
Microtubules / drug effects
Paclitaxel / analogs & derivatives
Paclitaxel / chemical synthesis*
Paclitaxel / pharmacology
Plant Leaves / chemistry
Plants, Medicinal / chemistry*
Taxoids*

Substances

Antineoplastic Agents, Phytogenic
Indicators and Reagents
Taxoids
Docetaxel
Paclitaxel