Research News

A paper entitled “Total Synthesis, Revised Structure, and Cytotoxic Activities of Iubol,” co-authored by Lecturer Keisuke Nishikawa and Professor Yoshiki Morimoto from the OMU Graduate School of Science, was published and featured on the front cover of “Chemistry Letters,” a journal in the field of chemistry.

Iubol is a marine cytotoxic bromotriterpenoid isolated from red alga. To unambiguously establish the three-dimensional structure of iubol, the researchers performed an asymmetric total synthesis, chemically synthesizing one of the optical isomers (enantiomers). The notable achievement of this research is that asymmetric epoxidation followed by cyclization was conducted in a one-pot process—a technique in which multiple reactions were carried out consecutively in just one reactor—to construct a six-membered ring ether at the end of the “natural product” portion of the synthesized product.

In this paper, the researchers reported the asymmetric total synthesis of iubol, corrected the erroneous part of the structural formula published in a previous study, and also discussed preliminary cytotoxic activities of synthetic compounds against several tumor cells.

The front cover features a science fiction scene, in which, when the correct structural formula is selected from several structural formulas floating in space and shot out with a “synthetic organic chemistry gun,” the beam wave is filled with cytotoxic activities against tumor cells of synthetic compounds, defeating a cancer cell army of UFOs!

Paper Information

Chem. Lett. 51, 1000-1003 (2022).

Funding

This work was financially supported by the Nagase Science Technology Foundation, the Suntory Foundation for Life Sciences Bioorganic Research Institute, and the Sasakawa Scientific Research Grant from the Japan Science Society.

Reference

Synthetic Organic Chemistry Laboratory

Contribution to SDGs

3: Good Health and Well-being
9: Industry, Innovation and Infrastructure

Media Contact

Graduate School of Science
Lecturer Keisuke Nishikawa
E-mail: knishi[at]omu.ac.jp
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