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Synthetic Medicinal Chemistry(Chemistry)

Akai ShujiProfessor

He received his Ph.D. degree in 1987 from Osaka University. After two years of research at Osaka University as a JSPS Research Fellow, he was appointed as an Assistant Professor at the university's Faculty of Pharmaceutical Sciences. During his tenure, he spent one year (1997-98) with Professor S. L. Buchwald at the Department of Chemistry, MIT, USA as a MEXT overseas research fellow. He was promoted to Full Professor in 2005 at the University of Shizuoka and returned to Osaka University as a Full Professor in 2013. He received the Inoue Research Award for Young Scientists (1987), the Pharmaceutical Society of Japan Award for Divisional Scientific Promotions (2003), and the Japan Society of Process Chemistry Awards (2005 and 2011).

Research theme

Synthesis and structural modification of novel functional organic compounds for drug discovery and medical treatment

Based on organic chemistry, we aim to synthesize highly functional organic compounds that are useful for drug discovery and medical treatment. To this end, we are also focusing on the development of new synthetic methods and catalysts for the rapid and convenient synthesis of natural organic compounds with unique chemical structures and remarkable biological activities, as well as their various derivatives. The project is characterized by the exploitation of untapped potential of representative elements, transition metals and enzymes, and the integration of their properties.

Development of an Environmentally Benign Asymmetric Synthesis Method Utilizing Hydrolases

Enzymes, which are born from nature through fermentation and return to it through degradation, exhibit extremely high chemoselectivity, stereoselectivity, and catalytic turnover at round room temperature and ordinary pressure. Therefore, they are one of the ideal catalysts for sustainable material production. We are working on the development of methods to construct chiral drug candidates with complex molecular structures by utilizing the excellent enantiodiscriminating ability of lipases, easy-to-handle hydrolases among diverse enzymes. Recent achievements include dynamic kinetic resolution, asymmetric desymmetrization, and synthesis of optically pure molecules by one-pot sequential reactions, developed by combining latest organic synthetic methods with enzymatic reactions.

Medicinal Chemistry Utilizing the Properties of Fluorine Atoms

The introduction of fluorine into bioactive compounds often improves their metabolic stability, membrane permeability, and other desirable properties as pharmaceuticals. Half of the fluorinated drugs currently on the market have fluorine substitutions in the benzene ring, but methods for introducing fluorine at desired positions in the benzene ring are still limited. To further expand the potential of small molecule drug discovery, We have developed a method to replace either one of the two hydroxyl groups in the catechol structure, which is often found as a structural motif in natural products, with fluorine at the desired position. By applying this method to natural products and synthetic compounds containing catechol moieties, the creation of novel drug discovery candidates is underway.

Regiocontrol and Synthetic Chemical Applications of Highly Reactive Benzynes

Benzynes, having a triple bond in the benzene ring, exhibit extremely high chemical reactivity and have been used for the one-step synthesis of polysubstituted and/or fused benzenes. However, it has been difficult to control the reaction positions of the benzynes. By introducing a boron, silicon, oxygen, or bulky substituent into the adjacent position of the benzyne’s triple bond, we have achieved the reaction site control as desired. Another advantage of this method is that the commanding substituents can be converted into other substituents in subsequent steps. This achievement paves the way for the fewer-step synthesis of a variety of polysubstituted and/or fused aromatic compounds by direct coupling of benzynes with other components. We are currently promoting research aimed at the practical application of this method.

Representative achievements

Could London Dispersion Force Control Regioselective (2 + 2) Cyclodimerizations of Benzynes? YES: Application to the Synthesis of Helical Biphenylenes
Takashi Ikawa,* Yuta Yamamoto, Akito Heguri, Yutaka Fukumoto, Tomonari Murakami, Akira Takagi, Yuto Masuda, Kenzo Yahata, Hiroshi Aoyama, Yasuteru Shigeta, Hiroaki Tokiwa,* and Shuji Akai*
J. Am. Chem. Soc. 2021, 143, 10853−10859.

Lipase-Catalyzed Dynamic Kinetic Resolution of C1- and C2-Symmetric Racemic Axially Chiral 2,2’-Dihydroxy-1,1’-biaryls
Gamal A. I. Moustafa, Yasuhiro Oki, Shuji Akai*
Angew. Chem. Int. Ed. 2018, 57, 10278 –10282.

Preparation of optically active cycloalkenes bearing all-carbon quaternary stereogenic centres via lipase–oxovanadium combo-catalysed dynamic kinetic resolution
S. Kawanishi, K. Sugiyama, Y. Oki, T. Ikawa, S. Akai*
Green Chem. 2017, 19, 411–417.

A Mesoporous-Silica-Immobilized Oxovanadium Cocatalyst for the Lipase-Catalyzed Dynamic Kinetic Resolution of Racemic Alcohols
M. Egi, K. Sugiyama, M. Saneto, R. Hanada, K. Kato, S. Akai*
Angew. Chem. Int. Ed. 2013, 52, 3654–3658.

ortho-Selective Nucleophilic Addition of Primary Amines to Silylbenzynes: Synthesis of 2-Silylanilines
T. Ikawa, T. Nishiyama, T. Shigeta, S. Mohri, S. Morita, S. Takayanagi, Y. Terauchi, Y. Morikawa, A. Takagi, Y. Ishikawa, S. Fujii, Y. Kita, S. Akai*
Angew. Chem. Int. Ed. 2011, 50, 5674–5677.

Preparation and Regioselective Diels–Alder Reactions of Borylbenzynes: Synthesis of Functionalized Arylboronates
T. Ikawa, A. Takagi, Y. Kurita, K. Saito, K. Azechi, M. Egi,K. Kakiguchi, Y. Kita, S. Akai*
Angew. Chem. Int. Ed. 2010, 49, 5563–5566

Synthesis of Biaryl Compounds through Three-Component Assembly: Ambidentate Effect of the tert-Butyldimethylsilyl Group for Regioselective Diels–Alder and Hiyama Coupling Reactions
S. Akai,* T. Ikawa, S. Takayanagi, Y. Morikawa, S. Mohri, M. Tsubakiyama, M. Egi, Y. Wada, Y. Kita
Angew. Chem. Int. Ed. 2008, 47, 7673–7676

Total Synthesis of (±)--Rubromycin on the Basis of Two Aromatic Pummerer-Type Reactions
S. Akai, K. Kakiguchi, Y. Nakamura, I. Kuriwaki, T. Dohi, S. Harada, O. Kubo, N. Morita, Y. Kita,
Angew. Chem. Int. Ed. 2007, 46, 7458–7461.

A Dynamic Kinetic Resolution of Allyl Alcohols by the Combined Use of Lipases and VO(OSiPh3)3
S. Akai,* K. Tanimoto, Y. Kanao, M. Egi, T. Yamamoto, Y. Kita,
Angew. Chem. Int. Ed. 2006, 45, 2592–2595.

Lipase-Catalyzed Domino Dynamic-Kinetic-Resolution of Racemic 3-Vinylcyclohex-2-en-1-ols/ Intramolecular Diels–Alder Reaction: One-Pot Synthesis of Optically Active Polysubstituted Decalines
S. Akai, K. Tanimoto, Y. Kita
Angew. Chem. Int. Ed. 2004, 43, 1407–1410.