Development of Stereoselective Construction of Fused Polycyclic Skeletons Containing Quaternary Asymmetric Carbon and Application to Synthetic Studies of Natural Products

2020 Fiscal Year Final Research Report

• Project/Area Number: 17K05857
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Niigata University
• Principal Investigator: SUZUKI Toshio 新潟大学, 自然科学系, 教授 (80202133)
• Project Period (FY): 2017-04-01 – 2021-03-31
• Keywords: 天然物合成 / 閉環反応 / 多環性骨格 / 縮環骨格 / Pentalenolactone F / Penifulvin A / Magellanine / Lycojaponicumin

Outline of Final Research Achievements

I have developed the methodology for construction of fused polycyclic skeletons based on the ring closure reactions of epoxy malonate, epoxy malononitrile, and epoxy phenol. Hydroxyl groups generated by cleavage of epoxides distinguish between two ester groups, cyano groups, or crossed dienones to form lactones, and asymmetric quaternary carbons were introduced by asymmetry of prochiral quaternary carbons. The methodologies were applied to synthetic studies of natural products consisting of fused polycyclic skeletons, Pentalenolactone F, Penifulvin A, Magellanine, Lycojaponicumin, and their related compounds.

Free Research Field

天然物化学

Academic Significance and Societal Importance of the Research Achievements

本研究で開発された方法論は，分子が有するエポキシドの不斉を利用したプロキラルな４級炭素の非対称化による不斉４級炭素の導入を含んだ，様々な多環性縮環骨格を立体選択的に構築する新しい手法である。また，様々な天然物の合成研究に適用し，その有用性を示した点で学術的意義がある。一方，本研究での成果は，生理活性・薬理活性を有する天然物の合成に活用されることが期待され，社会が求める有機化合物を容易に供給できることとなる点で社会的意義も大きい。