Development of novel cascade reactions for polysubstituted polycyclic aromatics

2022 Fiscal Year Final Research Report

• Project/Area Number: 20K06947
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
• Research Institution: Tokyo University of Pharmacy and Life Science
• Principal Investigator: YANAI Hikaru 東京薬科大学, 薬学部, 准教授 (10408685)
• Project Period (FY): 2020-04-01 – 2023-03-31
• Keywords: 有機合成化学 / カスケード反応 / 多環式芳香族炭化水素 / 蛍光分子 / 複素環式芳香族化合物

Outline of Final Research Achievements

Aromatic polyketides, which have polycyclic aromatic skeletons bearing various substituents on each carbon atom, have attracted attention in many fields of chemistry. However, such poly-substituted polycyclic structures are difficult to construct in a selective fashion. To cover the structural diversity of polycyclic aromatic compounds, we have studied a systematic development of novel cascade reactions from easily available lactol silyl ether (LSE) substrates. Careful choice of latently reactive functionalities on the LSE scaffold and detailed studies to find the effective reaction conditions provided effective reactions to yield less accessible 1,2,3,4-tetrasubstituted naphthalene derivatives in a selective manner. Furthermore, we evaluated unique photoluminescence properties of the polycyclic products thereby obtained.

Free Research Field

有機化学

Academic Significance and Societal Importance of the Research Achievements

従来法での合成が困難な多置換・多環式芳香族化合物を高収率かつ高選択的に与える複数のカスケード反応を開発し、ラクトールシリルエーテル構造上に置く潜在的な反応性官能基の選択から、置換パターンや置換基の種類にバリエーションをもたらすという新たな合成戦略の提案を行った。また、多置換・多環式芳香族骨格に起因する新たな分子機能を探求した結果、その特異な分子構造によって始めて分子機能が発現するケースを見いだすこともできた。従って、本研究成果は、合成法の欠如から十分な検討が行われていなかった新化合物群へのアクセスと確立しただけでなく、化学合成の戦略や機能分子の開発指針にも一定の波及効果をもつと考えている。