Toshiki Murayama (D2), Department of Chemistry and Biotechnology, wins a CSJ Student Presentation Award 2018

Toshiki Murayama (D2), Department of Chemistry and Biotechnology, wins a CSJ Student Presentation Award 2018.

Candidates are evaluated on presentation content, presentation ability, the quality of question and answer and overall presentation. Also, candidates are expected to progress the research strongly.

< About awarded research >

The deoxypropionate motif (i.e., 1,3,5,...,(2n−1)-polymethylalkyl chain) is a common substructure found in natural products. To construct the structure consisting of repeating units, a majority of the reported syntheses employ iterative reactions; long reaction sequences of 3–6 reactions per unit are typically necessary.

In this research, we demonstrated the single-step synthesis of syn- and anti-deoxypropionate motif. Asymmetric isospecific oligomerization of propylene catalyzed by optically active C₂-symmetric zirconocene complex proceeded in the presence of diethylzinc, and subsequently upon oxidation, the alcohol containing syn-deoxypropionate motif was isolated. This alcohol is the synthetic precursor of the wax secreted by graylag goose.

Conversely, syndiospecific oligomerization of propylene catalyzed by the C_S-symmetric zirconocene complex proceeded in the presence of di(n-propyl)zinc, and subsequently upon oxidation, the alcohol containing anti-deoxypropionate motif was isolated. This alcohol is the synthetic precursor of the hydrocarbon isolated from the cane beetle.

<Comments>

It is a great honor to receive the student presentation award. I would like to thank Prof. Kyoko Nozoki and lab members for their support.