formation of carbon four-membered rings using ynolate and its application for drug discovery

2023 Fiscal Year Final Research Report

• Project/Area Number: 21K05069
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: Hyogo Medical University (2022-2023); Kyoto University (2021)
• Principal Investigator: Yamaoka Yousuke 兵庫医科大学, 薬学部, 講師 (60624723)
• Project Period (FY): 2021-04-01 – 2024-03-31
• Keywords: イノラート / シクロブテン / 生理活性物質

Outline of Final Research Achievements

We have established a new method for the synthesis of ynolates and investigated the (2+2) cycloaddition of the ynolates with α,β-unsaturated carbonyl compounds to afford four-carbon rings. Cyclobutenes were efficiently synthesized by the ynolate generated from α,α,α-tribromomethylketone, which is easily prepared. This method showed a wide range of substrate scope. furthermore, we have also succeeded apply to the flow method. We are currently working on the synthesis of providencin as an application of this reaction.

Free Research Field

有機化学

Academic Significance and Societal Importance of the Research Achievements

新しい反応系の開発は、単純に新規反応の開発に貢献するだけでなく、より効率的な医薬品や生理活性物質の合成を可能とする。本研究では、容易に合成可能な試薬から多官能基化されたシクロブテンを効率的に合成できる。またフロー法により迅速かつ温和な条件にて合成できることも見出している。本手法を用いた有用天然物や医薬品の合成ならびにそれらの生物活性評価なども行い、実践的研究につなげていく予定である。