2018 Fiscal Year Final Research Report

Total synthesis of natural products by organocatalytic construction of all-carbon quaternary stereocenter

Research Project

PDF

Project/Area Number	16K17903
Research Category	Grant-in-Aid for Young Scientists (B)
Allocation Type	Multi-year Fund
Research Field	Synthetic chemistry
Research Institution	Meijo University (2017-2018) Kyoto University (2016)
Principal Investigator	Yoshida Keisuke 名城大学, 薬学部, 助教 (20709779)
Project Period (FY)	2016-04-01 – 2019-03-31
Keywords	有機合成化学 / 天然物化学 / 有機触媒 / 全合成
Outline of Final Research Achievements	There are many natural products and drugs including chiral spiro-ring. However, the construction of spiro-ring containing a quaternary carbon is more difficult than the spiro ring having a hetero atom. In our laboratory, we developed the new method using organocatalyst to construct the all-carbon quaternary stereocenter or tetrasubstituted carbon by intramolecular Friedel-Crafts type 1.4 addition reaction and oxy-Michel addition. Furthermore, we succeeded to apply these reactions into the total synthesis of (-)-misramine and（-)-(R)-cordiachromene.
Free Research Field	有機合成化学
Academic Significance and Societal Importance of the Research Achievements	申請者の開発した有機分子触媒によるエナンチオ選択的な不斉四級炭素構築法は、これまで光学活性体の合成報告例のない不斉四級炭素含有天然物が効率的に構築できる。そのため、天然からの供給が少なく、いまだ生物活性の報告例がない各種類縁体の合成が可能であり、新たな活性の発見や、医薬品シード化合物探索としての展開が期待できる。