Life Science and Technology News
Synthesis of Biologically Active Compounds
The Department has a variety of laboratories for Life Science and Technology, in which cutting-edge innovative research is being undertaken not only in basic science and engineering but also in the areas of medicine, pharmacy, agriculture, and multidisciplinary sciences.
This "Spotlight" series features a laboratory from the Department and introduces you to the laboratory's research projects and outcomes. This time we focus on Kobayashi Laboratory.
※Professor Kobayashi was retired on March 31, 2019.
Life Science and Technology
Professor Yuichi Kobayashi
|Degree||PhD 1981, Tokyo Institute of Technology|
|Areas of Research||Synthetic organic chemistry, Medicinal chemistry, Drug design|
|Keywords||Organic synthesis, Natural products, Pd-catalyzed reaction, C-C bond formation|
We are synthetic organic chemists and interested in synthesis of biologically important natural products that are hardly available from the natural sources. Synthetic design of targeted natural products are important step to achieve synthesis. We are also interested in carbon-carbon bond forming reactions using transition metals as reactants or catalysts. Furthermore, we have contributed to joint-research with biochemists using our compounds.
Resolvins are metabolites of eicosatetraenoic acid (EPA) and docosahexaenoic acid (DHA) that are potent mediators of anti-inflammatory activity. We use several asymmetric and stereoselective reactions to construct the structure. High selectivity and yields are advantage of our syntheses.
We have interested in the use of the mono-acetate of cyclopentene-1,3-diol as the starting compound, which are available as optically active compounds. We have developed several reagents that react at the α carbon bearing OAc or at the γ carbon (olefin end). We have used this reaction to synthesize 2-(epoxy-isoprostane)-phosphorylcholines isolated from atherosclerotic lesion and epi-jasmonates including isoleucin conjugate of epi-jasmonic acid. Furthermore, the cyclopentene ring was converted to the piperidine ring in the synthesis of quinine and quinidine.
We found the picolinoxy group is the highly reactive leaving group in the allylic substitution of secondary allylic esters with organocopper reagents. This leaving group allows the use of less reactive aryl, hetero-aryl, and alkynyl copper reagents. Furthermore, this reaction is extended to construct quaternary carbons.
We have successfully collaborated with compounds shown below.