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Synthetic Organic Chemistry for Drug Development(Chemistry)

Sako MakotoAssistant professor

Makoto Sako received his Ph.D. from the Graduate School of Sciences of Osaka University (Professor Hiroaki Sasai). In 2017, he became an assistant professor at SANKEN, Osaka University. In 2020, he moved as an assistant professor to the Graduate School of Pharmaceutical Sciences at Osaka University, where he works in the laboratory of Prof. Mitsuhiro Arisawa (2020 to present). His current research interests are focused on synthetic organic chemistry and the development of novel asymmetric catalysis.

Research theme

Development of novel asymmetric catalysts and application to catalytic asymmetric synthesis

Optically active compounds are widely utilized in the field of pharmaceuticals and pesticides. The aim of this research is to develop a new asymmetric catalyst for an innovation of a catalytic asymmetric synthesis technology that can produce a large amount of optically active compounds from a small amount of chiral source. We are also performing the design of catalyst molecules and the elucidation of reaction mechanisms using computational chemistry.

Development of efficient sequential reactions for the synthesis of novel polycyclic heterocyclic compounds

Heterocyclic compounds are often seen in pharmaceutical products, and their structural diversity is of interest to many researchers. The aim of this research is to synthesize a novel polycyclic heterocyclic compound based on a compound possessing a unique reactive structure for the purpose of creating small molecule drugs. We are also actively working on the development of practical synthetic processes using sequential reactions, and the acceleration of reaction development incorporating informatics.

Machine learning-assisted acceleration of organic reaction development

This research aims to accelerate the development of organic reactions through data-driven optimization of reaction conditions as a next-generation R&D process that realizes cost reduction.

Representative achievements

Axially Chiral Borinic Acid Catalysts: Design, Synthesis, and Application in Alkylative Desymmetrization of 1,2-Diols
Chikashige, Y.; Takehara, T.; Matsuzaki, T.; Suzuki, T.; Murai, K.; Arisawa, M.*; Sako, M.*
J. Org. Chem. 2023, 88, 14178-14183.

Heteroannulation of Bicyclobutane Derivatives via Au-catalyzed Hydration to Enol Ethers and Intramolecular Cyclization Giving Spirocyclobutanes
Takatsuki, M.; Aoyama, H.; Murai, K.; Arisawa, M.*; Sako, M.*
Chem. Commun. 2023, 59, 7467-7470.

Electrochemical Synthesis of Heterodehydro[7]helicenes
Khalid, Md. I.; Salem, M. S. H.; Sako, M.; Kondo, M.; Sasai, H.*; Takizawa, S.*
Commun. Chem. 2022, 5, 166.

Metal-free C(aryl)–P Bond Cleavage: Experimental and Computational Studies of the Michael Addition/aryl migration of Triarylphosphines to Alkynyl Esters
Sako, M.; Kanomata, K.; Salem, M. S. H.; Furukawa, T.; Sasai, H.; Takizawa, S.*
Org. Chem. Front. 2022, 9, 2187-2192.

Chemo- and Enantioselective Hetero-coupling of Hydroxycarbazoles Catalyzed by a Chiral Vanadium(v) Complex
Sako, M.; Higashida, K.; Kamble, G. T.; Kaut, K.; Kumar, A.; Hirose, Y.; Zhou, D.; Suzuki, T.; Rueping, M.; Maegawa, T.; Takizawa, S.*; Sasai, H.*
Org. Chem. Front. 2021, 8, 4878-4885.

Catalytic and Enantioselective oxa-Piancatelli Reaction Using Chiral Vanadium Complex
Schober, L.‡; Sako, M.‡; Takizawa, S.*; Gröger, H.*; Sasai, H.*
Chem. Commun. 2020, 56, 10151-10154. (‡equal contribution)

C−H Triflation of BINOL Derivatives Using DIH and TfOH
Nakazawa, H.; Sako, M.*; Masui, Y.; Kurosaki, R.; Yamamoto, S.; Kamei, T.; Shimada, T.*
Org. Lett. 2019, 21, 6466-6470.

Chiral Dinuclear Vanadium Complex-mediated Oxidative Coupling of Resorcinols
Sako, M.; Aoki, T.; Zumbrägel, N.; Schober, L.; Gröger, H.; Takizawa, S.*; Sasai, H.*
J. Org. Chem. 2019, 84, 1580-1587.

Short Syntheses of 4-Deoxycarbazomycin B, Sorazolon E, and (+)-Sorazolon E2
Sako, M.; Ichinose, K.; Takizawa, S.*; Sasai, H.*
Chem. Asian J. 2017, 12. 1305-1308.

Efficient Enantioselective Synthesis of Oxahelicenes Using Redox/Acid Cooperative Catalysts
Sako, M.; Takeuchi, Y.; Tsujihara, T.; Kodera, J.; Kawano, T.; Takizawa, S.*; Sasai, H.*
J. Am. Chem. Soc. 2016, 138, 11481-11484.