著者
大嶋 孝志 小池 隆司 笹野 裕介 高須 清誠 安田 誠 山口 潤一郎 菅 誠治 跡部 真人 外輪 健一郎 滝澤 忍 椴山 儀恵 矢島 知子 宮尾 知幸 小島 諒介 武田 和宏 松原 誠二郎 矢田 陽
出版者
九州大学
雑誌
学術変革領域研究(A)
巻号頁・発行日
2021-09-10

本領域研究は、有機合成に破壊的イノベーションを起こすデジタル有機合成(実験科学と情報科学の異分野融合)の基盤を世界に先んじて築くことを目的とし、有機合成の多様性に対応した独自のデジタル化プラットフォーム(PF)を構築する。A01班、A02班、A03班の3班体制で、人工知能(AI)を徹底活用した自動化法(分子構造自動設計、合成経路自動探索、反応条件自動最適化、バッチ→フロー自動変換、自律的自動合成システム)でムダを徹底排除し、革新反応・革新分子創出の超加速化を実現するとともに、自動化法開発の基盤となる、有機化学の機械学習に最適化した本領域独自のデータベース(DB)の構築を行う。
著者
須藤 絢音 山口 潤一郎
出版者
公益社団法人 有機合成化学協会
雑誌
有機合成化学協会誌 (ISSN:00379980)
巻号頁・発行日
vol.79, no.10, pp.910-967, 2021-10-01 (Released:2021-10-08)
参考文献数
592
被引用文献数
4

Fluorination is a well-studied organic reaction due to widespread applications of fluorine compounds for pharmaceuticals. In this review, we focus on the monofluorination reactions reported in the past ten years and describe in detail about versatile types of C-F bonds in the products, with particular classification on the type of the reaction and the catalyst.
著者
淺原 光太郎 柏原 美勇斗 武藤 慶 中尾 佳亮 山口 潤一郎
出版者
公益社団法人 有機合成化学協会
雑誌
有機合成化学協会誌 (ISSN:00379980)
巻号頁・発行日
vol.79, no.1, pp.11-21, 2021-01-01 (Released:2021-01-09)
参考文献数
108

Transition metal-catalyzed cross-coupling between aryl halides and nucleophiles is one of the most reliable C-C and C-heteroatom bond forming reactions. However, preparation of haloarenes usually requires multi-step operation, making the whole cross-coupling process inefficient. Nitroarenes, synthesized by a single-step nitration of arenes, can be attractive alternatives as electrophiles in cross-coupling methodology, but inherent inertness of C(sp2)-NO2 bonds toward metal catalysts has been a bottleneck of general denitrative transformations. Recently, we have overcome this obstacle and achieved direct activation of Ar-NO2 bonds by using Pd/BrettPhos catalysis. Herein, we describe the development of denitrative couplings by Pd/BrettPhos catalyst and its unique suitability from a mechanistic point of view. Deep understanding of reaction mechanism also enabled us to design more active Pd/NHC system.
著者
山口 潤一郎
出版者
公益社団法人 有機合成化学協会
雑誌
有機合成化学協会誌 (ISSN:00379980)
巻号頁・発行日
vol.76, no.5, pp.510-513, 2018-05-01 (Released:2018-05-12)
参考文献数
22

In 2048, the vast majority of occupations have been replaced by artificial intelligence (AI), we do not do the routine work anymore. In the research of natural product synthesis, it is scenery completely different from the research environment 30 years ago. Here, I anticipate how the synthesis of natural products changed in 30 years.
著者
山口 潤一郎 掛谷 秀昭 庄司 満 長田 裕之 林 雄二郎
出版者
天然有機化合物討論会
雑誌
天然有機化合物討論会講演要旨集
巻号頁・発行日
no.47, pp.25-30, 2005-09-15

Lucilactaene (1), a cell-cycle inhibitor in p53-Transfected cancer, is a synthetically challenging molecule because of its rare hexahydro-3a-hydroxy-5-oxo-2H-furo [3,2-b]pyrrol-6-yl ring system and its substituted and conjugated E,E,E,E,E pentaene moiety, which is unstable to acid, base, and light. Lucilactaene (1), which readily undergoes racemization, has been synthesized for the first time in optically pure form via a biomimetic pathway. The conditions under which racemization occurs were elucidated during this total synthesis. The careful isolation of lucilactaene (1) from both the broth and the mycelia under neutral, nonracemizing conditions demonstrated that the isolable natural product is in fact itself racemic. This total synthesis, which enabled verification of the absolute configuration of lucilactaene (1), has several noteworthy features: All the reactions from NG-391 (2) are mild enough not to affect the labile E,E,E,E,E pentaene moiety; ether formation from 2 to 25 and 28 and the intramolecular Michael reaction from 26 to 27 or from 30 to 31 are both highly stereoselective; the reductive removal of the epoxide with Sml_2 without effecting demethoxylation, andthe deprotection of a hemiaminal under neutral, oxidative conditions via vinyl ether 33 by using a newly developed phenylselenylethyl protecting group, are also useful transformations.