Synthesis and biological properties of naturally-occurring highly ordered quinoidal pigments

2022 Fiscal Year Final Research Report

• Project/Area Number: 20K06955
• 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: Tokushima Bunri University
• Principal Investigator: Kitamura Kei 徳島文理大学, 薬学部, 助教 (00756695)
• Project Period (FY): 2020-04-01 – 2023-03-31
• Keywords: ウロロイコナフィン / ビリダフィン / 二量体天然物 / ピラノナフトキノン / エクスホリアマイシン / C-グリコシド / 芳香族ポリケチド

Outline of Final Research Achievements

The syntheses of the hybridized aromatic polyketide natural products, 1) uroleuconaphins and viridaphins, the dimeric natural products, and 2) exfoliamycin, the C-glycoside antibiotic, have been studied.
1) The common monomeric units of uroleuconaphins and viridaphins were synthesized using an annulation of phthalide anion (Hauser-Kraus reaction) with optically active enone as a key step. In addition, the chemical transformations of the dimeric compounds under acidic or basic conditions were achieved. 2) The stereoselective synthesis of the aglycon and the construction of C-glycoside via 1,2-addition were developed.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

天然には同じ単量体構造を有するものの、その結合様式や酸化度の違いにより多様な複合構造を形成するものが多く存在する。本研究ではその基本構造となる単量体化合物を簡便に合成する方法を開発するとともに二量体化合物の化学変換による誘導化に成功した。今後、天然および非天然誘導体の合成への応用が期待される。