Development of Method for Molecular Transformations Based on Photoredox Reaction of Quinones

2017 Fiscal Year Final Research Report

• Project/Area Number: 26810018
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Tokyo Institute of Technology
• Principal Investigator: ANDO Yoshio 東京工業大学, 理学院, 助教 (40532742)
• Project Period (FY): 2014-04-01 – 2018-03-31
• Keywords: 有機合成化学 / キノン / 光化学反応 / 天然物 / 全合成

Outline of Final Research Achievements

Quinones are widely distributed in nature as pigments and bioactive molecules. Some quinones show particular reactivity under photo-irradiation. However, such reactivity has been overlooked and not been employed in organic synthesis so far.
In this research, a new synthetic method for organic compounds, which have been unachievable by conventional method, was developed by exploiting photoredox reaction of quinones. The substrate scope has been clarified. Moreover, it was found that the photoredox reaction proceeds with stereospecific manner. As the application, the first enantioselective total synthesis of spiroxin C, dimerized naphthoquinone natural product, has been accomplished by employing stereospecific photoredox reaction as the key step.

Free Research Field

有機合成化学