医薬品化学教室
医薬品化学教室
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環境にやさしい、医薬品の化学的合成法の開発をめざして
物質を安全に効率的に化学合成する技術は、現代の医薬品開発に欠かせない技術。私たちは有機金属錯体や有機分子を利用した人工酵素である「分子触媒」の開発で、従来は難しかった物質や医薬品をより簡単な方法で合成し、大量供給を目指します。しかもこれは省資源?省エネルギーな環境調和型の合成技術なのです。
卒業後進路 就職先 のページヘ
これまでに下記の学生を受け入れております。
博狗体育在线_狗博体育直播【官方授权网站】@ 薬学部 生命創薬科学科
博狗体育在线_狗博体育直播【官方授权网站】@ 理学部 化学科
東京薬科大学 生命科学部
明治薬科大学 薬学部 生命創薬科学科
横浜薬科大学 薬科学科
有機化学に興味を持ち、熱意ある大学院生を広く歓迎しております。
業績
Manganese-Catalyzed 5-Endo-trig Oxygenative Cyclization of α,β-Unsaturated Oximes under Air and Ambient Conditions for the Synthesis of 4,5-Dihydroisoxazoles
J. Org. Chem. 2024, 89, 9, 6377–6388
Daisuke Yamamoto,* Daisuke Matsukawa, Ryusei Kikuchi, Yuki Narushima, Yuta Kumakura, Mana Ito, and Kazuishi Makino*
The stereoselective 5-endo-trig oxygenative cyclization of α,β-unsaturated oximes was achieved using molecular oxygen (O2) and a manganese catalyst. Several 4-hydroxy-4,5-dihydroisoxazoles were obtained in high yields by directly incorporating O2 from the atmosphere (eliminating the necessity for a pure oxygen environment) and using an unprecedentedly low loading of Mn(acac)3 (as little as 0.020 mol %) without additional additives. Because of its desirable features, such as operational simplicity, inexpensive catalyst, mild reaction conditions (open flask conditions at room temperature), and broad substrate compatibility, this novel reaction provides an attractive synthetic approach to producing 4-hydroxy-4,5-dihydroisoxazoles.
Stereoselective synthesis of the isoxazolidine ring via manganese(iii)-catalysed aminoperoxidation of unactivated alkenes using molecular oxygen in air under ambient conditions
Green. Chem. 2022, 24, 7162-7170.
Yamamoto, D.*; Hirano, I.; Narushima, Y.; Soga, M.; Ansai, H.; Makino, K.*
In this study, we developed a route for the tris(mono-ferrocene-functionalised β-diketonato) manganese(III)-complex catalysed diastereoselective oxygenative aminoperoxidation of unactivated alkenes using molecular oxygen in air. In the reaction, ethanol is used as a solvent, and it proceeds at room temperature under open air. Due to its wide range of substrate scope, functional tolerance, simple operation and mild and environmentally friendly conditions, the reaction is a promising synthetic approach for synthesising valuable isoxazolidine rings as not only privileged structures in natural products but also versatile synthons for 1,3-amino alcohols.
Direct Synthesis of N-Protected Serine- and Threonine-Derived Weinreb Amides via Diboronic Acid Anhydride-Catalyzed Dehydrative Amidation: Application to the Concise Synthesis of Garner’s Aldehyde
Shimada, N.*; Ohse,N.; Takahashi, N.; Urata, S.; Koshizuka, M. Makino, K.
Synlett (2021), 32(10),1024-1028.
Boronic Acid-Catalyzed Final-Stage Site-Selective Acylation for the Total Syntheses of O-3'-Acyl Bisabolol β-D-Fucopyranoside Natural Products and Their Analogues.
Nakamura, Y.; Ochiai, T.; Makino, K.; Shimada, N.*
Chemical & Pharmaceutical Bulletin (2021), 69(3), 281-285
Boronic Acid-Catalyzed Regioselective Koenigs-Knorr-Type Glycosylation
Shimada, N.*; Sugimoto, T.; Noguchi, M.; Ohira, C.; Kuwashima, Y.; Takahashi, N.; Sato, N.; Makino, K.
Journal of Organic Chemistry (2021), 86(8), 5973-5982
Synthesis of Weinreb amides using diboronic acid anhydride-catalyzed dehydrative amidation of carboxylic acids
Shimada, N.*; Takahashi, N.; Ohse, N.; Koshizuka, M.; Makino, K.
Chemical Communications (Cambridge, United Kingdom) (2020), 56(86), 13145-13148
Diboronic acid anhydride-catalyzed direct peptide bond formation enabled by hydroxy-directed dehydrative condensation
Koshizuka, M.; Makino, K.; Shimada, N.*
Organic Letters (2020), 22(21), 8658-8664
Total syntheses of seminolipid and its analogues by using 2,6-bis(trifluoromethyl)phenylboronic acid as protective reagent
Shimada, N.*; Fukuhara, K.; Urata, S.; Makino, K.*
Organic & Biomolecular Chemistry (2019), 17(31), 7325-7329