Faculty Profiles - SATO Eisuke

Papers - SATO Eisuke

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Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis Reviewed

Eisuke Sato, Mayu Fujii, Hiroki Tanaka, Koichi Mitsudo, Masaru Kondo, Shinobu Takizawa, Hiroaki Sasai, Takeshi Washio, Kazunori Ishikawa, Seiji Suga

The Journal of Organic Chemistry 86 ( 22 ) 16035 - 16044 2021.11

Language：English Publishing type：Research paper (scientific journal) Publisher：American Chemical Society (ACS)

Cyanosilylation of carbonyl compounds provides protected cyanohydrins, which can be converted into many kinds of compounds such as amino alcohols, amides, esters, and carboxylic acids. In particular, the use of trimethylsilyl cyanide as the sole carbon source can avoid the need for more toxic inorganic cyanides. In this paper, we describe an electrochemically initiated cyanosilylation of carbonyl compounds and its application to a microflow reactor. Furthermore, to identify suitable reaction conditions, which reflect considerations beyond simply a high yield, we demonstrate machine learning-assisted optimization. Machine learning can be used to adjust the current and flow rate at the same time and identify the conditions needed to achieve the best productivity.

DOI： 10.1021/acs.joc.1c01242

Web of Science

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Synthesis of Morphinans through Anodic Aryl‐Aryl Coupling Reviewed

Nina Vierengel, Leander Geske, Eisuke Sato, Till Opatz

The Chemical Record 21 ( 9 ) 2344 - 2353 2021.9

Cu-Catalyzed Dehydrogenative C–O Cyclization for the Synthesis of Furan-Fused Thienoacenes Reviewed

Koichi Mitsudo, Yoshiaki Kobashi, Kaito Nakata, Yuji Kurimoto, Eisuke Sato, Hiroki Mandai, Seiji Suga

Organic Letters 23 ( 11 ) 4322 - 4326 2021.6

Electrosynthesis of Phosphacycles via Dehydrogenative C–P Bond Formation Using DABCO as a Mediator Reviewed

Yuji Kurimoto, Jun Yamashita, Koichi Mitsudo, Eisuke Sato, Seiji Suga

Organic Letters 23 ( 8 ) 3120 - 3124 2021.4

Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products Reviewed

Till Opatz, Leander Geske, Eisuke Sato

Synthesis 52 ( 19 ) 2781 - 2794 2020.10

Language：English Publishing type：Research paper (scientific journal) Publisher：Georg Thieme Verlag KG

Electrochemistry provides a valuable toolbox for organic synthesis and offers an appealing, environmentally benign alternative to the use of stoichiometric quantities of chemical oxidants or reductants. Its potential to control current efficiency along with providing alternative reaction conditions in a classical sense makes electrochemistry a suitable method for large-scale industrial transformations as well as for laboratory applications in the synthesis of complex molecular architectures. Even though research in this field has intensified over the recent decades, many synthetic chemists still hesitate to add electroorganic reactions to their standard repertoire, and hence, the full potential of preparative organic electrochemistry has not yet been unleashed. This short review highlights the versatility of anodic transformations by summarizing their application in natural product synthesis.

1 Introduction

2 Shono-Type Oxidation

3 C–N/N–N Bond Formation

4 Aryl–Alkene/Aryl–Aryl Coupling

5 Cycloadditions Triggered by Oxidation of Electron-Rich Arenes

6 Spirocycles

7 Miscellaneous Transformations

8 Future Prospects

DOI： 10.1055/s-0040-1707154

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Design, synthesis and anti-malarial activities of synthetic analogs of biselyngbyolide B, a Ca2+ pump inhibitor from marine cyanobacteria Reviewed

Eisuke Sato, Maho Morita, Haruo Ogawa, Masato Iwatsuki, Rei Hokari, Aki Ishiyama, Satoshi Ōmura, Arihiro Iwasaki, Kiyotake Suenaga

Bioorganic & Medicinal Chemistry Letters 28 ( 3 ) 298 - 301 2018.2

Language：English Publishing type：Research paper (scientific journal) Publisher：Elsevier BV

Biselyngbyaside, an 18-membered macrolide glycoside from marine cyanobacteria, and its derivatives are known to be sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) inhibitors. Recently, a SERCA orthologue of the malaria parasite, PfATP6, has attracted attention as a malarial drug target. To provide a novel drug lead, we designed new synthetic analogs of biselyngbyolide B, the aglycone of biselyngbyaside, based on the co-crystal structure of SERCA with biselyngbyolide B, and synthesized them using the established synthetic route for biselyngbyolide B. Their biological activities against malarial parasites were evaluated. (C) 2017 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2017.12.050

Web of Science

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Total Synthesis of Biselyngbyaside Reviewed

Eisuke Sato, Miho Sato, Yurika Tanabe, Naoya Nakajima, Akifumi Ohkubo, Kiyotake Suenaga

The Journal of Organic Chemistry 82 ( 13 ) 6770 - 6777 2017.7

Total Synthesis of Biselyngbyolide B Reviewed

Eisuke Sato, Yurika Tanabe, Naoya Nakajima, Akifumi Ohkubo, Kiyotake Suenaga

Organic Letters 2016.5

Total Synthesis of Biselyngbyolide A Reviewed

Yurika Tanabe, Eisuke Sato, Naoya Nakajima, Akifumi Ohkubo, Osamu Ohno, Kiyotake Suenaga

Organic Letters 2014.6

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