Development of new bond-forming methods based on the creation of highly reactive cyclic hypervalent iodine reagents

2021 Fiscal Year Final Research Report

• Project/Area Number: 19K06977
• 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: Gifu Pharmaceutical University
• Principal Investigator: Tada Norihiro 岐阜薬科大学, 薬学部, 講師 (20468234)
• Co-Investigator(Kenkyū-buntansha): 伊藤 彰近 岐阜薬科大学, 薬学部, 教授 (10203126)
• Project Period (FY): 2019-04-01 – 2022-03-31
• Keywords: 超原子価ヨウ素 / アミノ酸 / ペプチド / エチニル / ビニル

Outline of Final Research Achievements

Based on the synthesis of new cyclic hypervalent iodine compounds, we have developed new bond-forming methods that utilize the high reactivity of hypervalent iodine compounds. Specifically, various solvent complexes of ethynylbenziodoxolone were developed. By using highly reactive ethynylbenziodoxolone, we developed ethynylation reactions of sulfonamides derived from amino acids and peptides under mild conditions. Copper-catalyzed alkynylation of sulfonamides derived from amino acids and peptides under mild conditions was developed. Vinylation reactions of sulfonamides and hydroxamic acid derivatives derived from amino acids and peptides and phenols under mild conditions were developed.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

近年、創薬化学の分野では従来の低分子医薬品よりも分子量が大きく複雑な構造の中分子医薬品や高分子医薬品の開発が盛んに行われており、温和な条件下、複雑な分子に適用可能な化学選択的結合構築法の開発が望まれている。今回、高反応性の環状エチニル超原子価ヨウ素化合物を合成し、医薬品、天然物、アミノ酸、ペプチドなどの複雑分子を温和な条件で化学選択的にアルキニル化およびアルケニル化する反応を開発した。