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Synthesis of an Anticancer Agent using an Environmentally-friendly catalyst

Development of a Safe Osmium Catalyst for Industrial Applications

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Graduate School of Science / Faculty of Science
2012/08/22

One mol-scale synthesis of an intermediate of the anticancer drug camptothecin using a new immobilized osmium catalyst (PI Os)
© Sh? Kobayashi

A research group lead by Prof. Kobayashi at the University of Tokyo’s Graduate School of Science has developed an environmentally-friendly polymer-supported osmium catalyst (PI Os) by immobilizing osmium tetroxide on a polymer. Osmium tetroxide is useful as a catalyst of dihydroxylation reactions, but is difficult to employ in industrial applications because it is highly toxic and volatile. The research group succeeded in developing the nontoxic catalyst by immobilizing osmium tetroxide through a novel immobilization method (polymer-incarcerated method, or PI method). The research group has demonstrated the utility of the new catalyst through the industrial-scale synthesis of an intermediate of camptothecin, an anticancer agent. This is the first example of the use of an immobilized osmium catalyst for an industrial-scale process. It is strongly expected that the use of this catalysis method will improve the efficiency and reduce the environmental impact of many chemical processes which employ osmium as a catalyst. The result is important from the viewpoint of green sustainable chemistry since it provides an example of the conversion of a toxic agent to a nontoxic agent and demonstration of its application to an industrial-scale process. It is strongly expected that this method will be applied to other toxic agents in the future.

Press release (Japanese)

Paper

Ryo Akiyama, Norio Matsuki, Hiroshi Nomura, Hisao Yoshida, Tomoko Yoshida, and Sh? Kobayashi,
“Nontoxic, Nonvolatile, and Highly Efficient Osmium Catalysts for Asymmetric Dihydroxylation of Alkenes and Application to One Mol-scale Synthesis of an Anticancer Drug, Camptothecin Intermediate”,
RSC Advances, doi: 10.1039/C2RA21123H
Article link

Links

Graduate School of Science

Department of Chemistry

Synthetic Organic Chemistry Laboratory

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