著者

大野 祥平 有澤 光弘

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.22-33, 2021-01-01 (Released:2021-01-09)

参考文献数

50

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Cyclization reactions between two multiple bonds have been fascinating processes that allow the discovery of new reactions and the construction of carbo- and/or heterocycles. Among multiple bonds, heteroatom-substituted olefins have different reactivity from those having heteroatom on the allylic or homoallylic position, but the reactions have been reported few cases until the 2000s. Lately, the reactions between multiple bonds and heteroatom-substituted olefins have been reported, and this review explains them by the reaction class.

著者

田中 津久志 矢崎 亮 大嶋 孝志

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.5, pp.417-426, 2021-05-01 (Released:2021-05-11)

参考文献数

72

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Enolization of carboxylic acid derivatives is the central science of fundamental carbonyl chemistry. The catalytic methods to activate carboxylic acid remained unexplored due to the intrinsic low acidity of α-protons, although enormous examples of catalytic activation (enolization) method for aldehydes, ketones, and ester derivatives have been reported. The innate Brønsted acidic carboxylic acid functionality also disrupts the deprotonation of α-protons. Therefore, more than two equivalents of a strong base such as lithium diisopropylamide are required for efficient enolization, which makes chemoselective enolization of carboxylic acid over more acidic carbonyls a formidable task. Furthermore, recent enolization methods were only applied to redox-neutral coupling using 2e- electrophiles and catalytic α-functionalization of carboxylic acids through a 1e- radical process, which could complement the chemoselectivity, and functional group tolerance restricted in the classical 2e- ion reaction, has never been achieved. Herein, we developed chemoselective catalytic activation of carboxylic acid equivalent, acylpyra-zole, and carboxylic acid for a 1e- radical process without external addition of stoichiometric amounts of Brønsted base. The present chemoselective catalysis could be applied to late-stage α-amination and oxidation, allowing for concise access to highly versatile unnatural α-amino acid and hydroxy acid derivatives. Moreover, chemoselective α-functionalization of less reactive carboxylic acids was achieved over innately more reactive carbonyl functionalities.

著者

赤井 周司

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.2, pp.99, 2021-02-01 (Released:2021-02-10)

著者

小池 隆司 佐藤 伸一 久保 孝史 安倍 学

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.77, no.5, pp.514, 2019

著者

荒井 緑

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.56-58, 2021-01-01 (Released:2021-01-09)

著者

若木 重敏

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.21, no.2, pp.143-147, 1963-02-01 (Released:2010-06-28)

被引用文献数

1

著者

君嶋 葵

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.78, no.9, pp.901-903, 2020-09-01 (Released:2020-09-10)

参考文献数

8

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Hippolachnin is a polyketide natural product isolated from the marine sponge Hippospongia lachnein in China 2013, which has shown highly potent antibacterial activities against several pathogenic fungi. It features a highly substituted cyclobutane, six contiguous stereocenters, one of which is quaternary carbon and bears an unusual array of four ethyl groups on its convex face. In this review, total syntheses of hippolachnin by four groups are described.

著者

長沢 正雄

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.22, no.3, pp.170-176, 1964-03-01 (Released:2010-06-28)

参考文献数

15

著者

北 将樹

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.77, no.4, pp.371-373, 2019-04-01 (Released:2019-04-08)

著者

田中 遼

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.69, no.8, pp.937-938, 2011-08-01 (Released:2011-10-03)

参考文献数

6

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The C (aryl) -O bond formation was generally carried out by using transition metal-catalyzed coupling reaction between aryl halide and alcohol. Among them, Cu-mediated Ullmann reaction is a powerful method for the preparation of alkyl aryl ether from secondary alcohol. In this article, recent advances in Ullmann reaction are reviewed being categorized into two parts: ligand and aryl donor.

著者

篠崎 平馬 鈴木 満之助

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.2, no.4, pp.345-349, 1944-04-01 (Released:2010-10-20)

著者

田中 克典

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.10, pp.1110-1112, 2018-10-01 (Released:2018-10-09)

参考文献数

1

著者

田中 健太 星野 雄二郎 本田 清

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.12, pp.1341-1351, 2018-12-01 (Released:2018-12-12)

参考文献数

104

被引用文献数

6 8

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Condensed oxygen-heteropolycyclic compounds are one of attractive synthetic targets in organic synthetic chemistry. Among these useful compounds, chromenes and benzofurans are important structural motifs, which are found in a wide range of biologically active compounds and photochemical materials. Therefore, a number of research groups have developed methodologies to synthesize these compounds. ortho-Quinone methides are key reactive intermediates with a wide range of applications in organic synthesis. In this account, our recent research on acid-promoted inverse-electron-demand [4+2] cycloaddition reaction of electron-rich arylalkynes with ortho-quinone methides is described. This reaction can be applied to a variety of arylalkynes, affording high regioselective cycloadducts. The present reactions provide versatile access to functionalized multi-substituted chromenes and benzofurans, that would be a useful tool for the synthesis of biologically and photochemically active molecules.

著者

森 敦紀

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.78, no.3, pp.189, 2020-03-01 (Released:2020-03-07)

著者

千葉 一裕

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.78, no.2, pp.97, 2020-02-01 (Released:2020-02-08)

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

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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

都築 洋次郎

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.2, no.10, pp.604-614, 1944-10-01 (Released:2010-10-20)

著者

安藤 香織

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.77, no.10, pp.959, 2019-10-01 (Released:2019-10-09)

被引用文献数

3

著者

坂田 健 西林 仁昭 堀野 良和 吉田 昌裕 野口 誉夫 新海 征治

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.75, no.1, pp.66, 2017-01-01 (Released:2017-01-25)

被引用文献数

1 1

著者

伊藤 繁和

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.77, no.8, pp.800-812, 2019-08-01 (Released:2019-08-09)

参考文献数

72

被引用文献数

1

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The positive muon (µ+) is an elementary subatomic particle that is assigned as a member of lepton (spin I=1/2). Whereas muons are present in cosmic radiation, high-energy beam of proton from accelerators such as cyclotron and synchrotron produce almost fully polarized muons. The muon has one ninth of the proton mass (0.1126mp), and the polarized “ultralight proton” is applicable to similar spectroscopic analyses to electron-spin resonance (ESR) and nuclear magnetic resonance (NMR) without the alternative magnetic resonance techniques. In contact with matter, the positive muon captures an electron and become a muonium (Mu= [µ+e-]) that is a light isotope of hydrogen atom. The muoniums have been utilized for monitoring radical reactions of usual unsaturated organic molecules including benzene, alkene, alkyne, and ketone, and the corresponding radicals via muonium addition can be characterized by muon spin rotation/resonance/relaxation (µSR) spectroscopy. In this article, principles and usefulness of µSR for study of functional organic compounds are overviewed, and our recent findings on µSR measurements for the sterically encumbered 1,3-diphosphacyclobutane-2,4-diyl of singlet biradical are presented. A regioselective addition of muonium to the skeletal phosphorus atom in the 1,3-diphosphacyclobutane-2,4-diyl unit was characterized, which would be useful to understand the 4-membered heterocyclic molecular skeleton promoting the low-voltage p-type organic semiconductor behavior.