Synthetic Studies of Indole Terpenes Natural Products Toward the Derivatization of the Heterocyclic Ring to Luminescent Probes

2021 Fiscal Year Final Research Report

• Project/Area Number: 18K05460
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 38040:Bioorganic chemistry-related
• Research Institution: University of Toyama (2020-2021); Nara Institute of Science and Technology (2018-2019)
• Principal Investigator: Hiroki Tanimoto 富山大学, 学術研究部薬学・和漢系, 准教授 (00581331)
• Project Period (FY): 2018-04-01 – 2022-03-31
• Keywords: 天然物合成 / 誘導体合成 / テルペン / 化学プローブ

Outline of Final Research Achievements

We have established a concise and rapid synthesis of terpene skeletons of the natural product toward the derivatization of natural products composed of heterocyclic rings and terpene moieties. For the terpene moiety of the natural product, The initial route was limited to a few hundred milligrams in 30 h but was successfully improved to a few grams in about three hours. This route facilitates the large-scale supply of the molecules. For heterocyclic main group element moiety, synthesis and characterization of biologically active pentacoordinate silicon compound was also carried out. Furthermore, a flexible molecular coupling by the new click strategy was developed. Overall, we established new molecular technologies that contribute to the rapid synthesis of functional molecules possessing bioactivity and probe activity.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

生物活性分子の生体組織内での作用機構解明につながる分子の迅速な合成と、評価の指標になる発光分子などとの多様な連結による機能化技術を確立した。多くの研究者に分子モチーフを提供できる合成経路の確立、水素結合による連結反応の簡素な分子による高度な制御、ならびに典型元素による炭素原子ではできない構造による生物活性分子の可能性の発見は、広く創薬や高分子材料などの機能化ならびに迅速創出に利用できる基盤技術として大きく貢献するものである。