著者

長谷川 真士

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.78, no.11, pp.1066-1075, 2020-11-01 (Released:2020-11-07)

参考文献数

59

被引用文献数

1

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In general, cyclization is the most crucial step in the synthesis of macrocyclic compounds formed out of repeated units of a π-system. However, a particular combination of aromatic wall unit and appropriate angular linkage can efficiently give cyclic compounds such as calix[n]arene and its analogues. This straightforward method allows material chemists to supply these compounds on multi-gram scale. Nevertheless, a more resourceful strategy is also required, because this simple approach is less feasible outside of specific combinations. Recently, we have newly developed a straightforward one-pot synthetic approach using a palladium coupling for a series of thiacalix[n]thiophene, thiacalix[n]dithieno[3,2-b:2’,3’-d]thiophene (thiacalix[n]DTT), and selenacalix[n]selenophenes, which are cyclic homologues of divalent chalcogen-bridged (S or Se) cyclic oligothiophene derivatives. A palladium-catalyzed reaction of (Bu3Sn)2S or (Bu3Sn)2Se with dibromothiophene, dibromoselenophene, or diboromo-DTT derivatives led to effective cyclization in good yield. In the presence of appropriate substituents, this method seems to kinetically favor the formation of macrocycles. The molecular and physical properties, including X-ray analysis, absorption spectra and redox properties, of the resultant macrocycles were also described. Unlike conventional calixarenes, they possess electron-donating ability, exhibiting multielectron redox processes due to electron delocalization. Thiacalix[n]DTT derivatives (n=4-6) acted as a cavitand for C60 molecules; the cyclic 4-mer formed a 1:2 complex in the solid state, while the 5- and 6-mer formed 1:1 complexes in solution. Furthermore, thiacalix[4]thiophene and selenacalix[n]-selenophene having tert-butylphenyl groups exhibit gelling behavior in toluene, despite the absence of any hydrogen binding sites. Intermolecular chalcogen (S or Se) interactions facilitate the self-assembly that results in this gel formation.

著者

大宮 寛久

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.7, pp.732-734, 2019-07-01 (Released:2019-07-08)

著者

谷口 剛史

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.6, pp.584-595, 2019-06-01 (Released:2019-06-11)

参考文献数

41

被引用文献数

1

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The Mitsunobu reaction is widely used for transformation of hydroxy groups into various functional groups and inversion of the stereochemistry of secondary alcohols in organic synthesis. The Mitsunobu reaction, however, has some serious problems that inhibit its application of the reaction to practical synthesis on large scales. Especially, the reaction requires hazardous azo reagents such as diethyl azodicarboxylate (DEAD) and produces large amounts of undesired waste that sometimes complicate purification of the desired products. We have recently developed catalytic Mitsunobu reactions using new azo reagents recyclable by iron-catalyzed aerobic oxidation. Ethyl 2-(3,4-dichlorophenyl)hydrazinecarboxylate and ethyl 2-(4-cyanophenyl)hydrazinecarboxylate (or their azo forms) were identified as good catalysts by our systematic investigation. The modified catalytic reaction using these azo reagents was applicable to broad scope of substrates. High thermal stability of the reagents was shown by SC-DSC analysis, suggested low explosive nature of these reagents.

著者

西山 久雄

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.77, no.2, pp.189-191, 2019-02-01 (Released:2019-02-08)

参考文献数

16

被引用文献数

1

著者

畑 一夫

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.37, no.2, pp.148-160, 1979-02-01 (Released:2010-01-22)

参考文献数

5

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Complicated polycylic compounds often appear in recent chemical studies. This review explains the nomenclature of those polycyclic compounds-fused ring systems, bridged ring systems, and spiro ring systems.Although the nomenclatures of polycyclic hydrocarbons and heterocycles are provided under a common principle, the IUPAC rule book describes them separately in Section A and B. Since this separate description makes difficult to understand the nomenclature, this review gives a package explanation which covers both hydrocarbons and heterocycles. Cited apt examples will be useful rather than the text of the nomenclature rule.

著者

Takashi Nakanishi

出版者

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.72, no.11, pp.1265-1270, 2014-11-01 (Released:2014-12-19)

参考文献数

30

被引用文献数

2

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Room temperature liquid formulation of intrinsically stiff, optically or optoelectronically active, π-conjugated molecules, such as anthracenes, oligo(p-phenylenevinylenes), and fullerenes, by attaching soft branched long-alkyl chains is demonstrated. Multiple modification with the branched long-alkyl chains on the periphery of an emissive π-conjugated moiety results in isolation of the π-unit core, thus generating a room temperature liquid state with almost no π-π interaction among the adjacent π-units and which shows considerably good luminescence. When only partially wrapping a π-unit core, e.g. C60, attached by branched alkyl chains, those alkyl-π compounds are liquid/amorphous at room temperature, which however, can be directed into assembly by adding either of their own molecular segments, the π-unit or the alkyl-unit (alkane solvents). These ordered materials change from non-photoconductive monomer species to photoconductive assemblies.

著者

櫻井 高景

出版者

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.3, no.1, pp.27-35, 1945-01-01 (Released:2010-10-20)

著者

岩渕 好治

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.81, no.6, pp.626-629, 2023-06-01 (Released:2023-06-07)

参考文献数

9

著者

小原 正美 日野 哲雄

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.20, no.7, pp.676-687, 1962-07-01 (Released:2010-06-28)

参考文献数

53

著者

大東 篤 渡辺 勝 椋田 隆司

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.64, no.12, pp.1294-1303, 2006-12-01 (Released:2010-10-20)

参考文献数

8

被引用文献数

1 2

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The manufacturing process of Micafungin (1) which is a novel candin antifungal agent discovered and developed by Astellas Pharma Inc. was studied.A new asymmetric isoxazole ring formation which is key reaction for synthesis of side chain active ester 2 was developed via β-keto enamine intermediate.And also a reaction condition of selective acylation with FUN intermediate 3 and purification of Micafungin drug substance was investigated from the viewpoints of high quality and productivity.

著者

森 美和子

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.58, no.5, pp.511-513, 2000-05-01 (Released:2009-11-13)

著者

千田 憲孝

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.80, no.3, pp.282-285, 2022-03-01 (Released:2022-03-09)

参考文献数

26

著者

二木 鋭雄

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.47, no.10, pp.902-915, 1989 (Released:2010-01-22)

参考文献数

94

被引用文献数

14 19

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Vitamin E acts as a potent and safe, lipid-soluble antioxidant by scavenging primarily chain-carrying peroxyl radical and interrupting chain sequence. Four kinds of tocopherols and also four kinds of tocotrienols are known as vitamin E. Various kinds of vitamin E related compounds have been synthesized and their antioxidant activities have been compared. It was stressed that the antioxidant activities in vivo are determined not only by their inherent reactivities toward oxygen radicals but also by their local concentrations at a specific site where the oxidations are taking place.

著者

鈴木 啓介

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.1, pp.67-71, 2020-01-01 (Released:2020-01-10)

参考文献数

7

著者

友重 秀介

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.3, pp.264-266, 2019-03-01 (Released:2019-03-07)

参考文献数

9

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Bacteria possess a cell wall based on a rigid extracellular matrix comprised of peptidoglycan (PG), which maintains their structural integrity. Although PG is a molecule that has attracted interest from various research fields, such studies have been limited by the difficulty to isolate the desired PG fragments. In order to make PG fragments available, many efforts have been made to achieve their synthesis. This review summarizes the synthetic strategies reported for the construction of PG fragments by the Fukase and Fujimoto’s group as well as the Mobashery’s group. Furthermore, applications of synthetic PG fragments in chemical biology are described.

著者

中村 栄一

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.76, no.11, pp.1232-1246, 2018-11-01 (Released:2018-11-09)

参考文献数

105

被引用文献数

1

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This essay summarizes a personal history of studies on fluoride-mediated reactions of enol silyl ethers, metal homoenolate, cytochalasin and cortisone synthesis, cycloaddition chemistry of cyclopropenone acetals and dipolar trimethylenemethanes, biological activity of organofullerenes and DNA and siRNA delivery, organocuprate(I) reaction mechanisms, iron-catalyzed cross coupling and C-H activation reactions, 15O labeling for positron emission tomography (PET), functional fullerene molecules including bucky ferrocene, shuttlecock molecules and [10]cyclophenacene, fullerene bilayer vesicles, new design materials for organic and lead perovskite solar-cell fabrication, carbon-bridged oligophenylene vinylenes and single-molecule atomic-resolution real-time transmission electron microscopy (SMART-EM) for structural and kinetic studies of molecules and molecular clusters. It also describes how the encounters with key people may change the course of your scientific research as well as of your personal life. These examples suggest that life is a stochastic process, and, moreover, science in the future would be something that we do not even imagine now as a subject of research.

著者

武藤 慶

出版者

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.74, no.12, pp.1225-1226, 2016-12-01 (Released:2016-12-20)

参考文献数

12

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Dihalogenation of alkene is well known reaction undergoing in a stereospecific manner. Although enantioselective dihalogenation of alkene using chiral auxiliary was developed, the catalytic protocol remained as a challenging issue. This review summarizes recent progress of catalytic enantioselective dihalogenation of alkene.

著者

西村 吉雄

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.45, no.9, pp.873-887, 1987-09-01 (Released:2009-11-13)

参考文献数

81

被引用文献数

2 3

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This article describes the syntheses and the relationships between structure and antitumor activity of pyrrolizidine alkaloid (indicine N-oxide), lignan lactone glycoside (etoposide) and their related compounds from the standpoint of diastereomer and enantiomer.Total syntheses of indicine N-oxide, its diastereomer (intermedine N-oxide) and their enantiomers have been achieved in a totally stereospecific fashion through a sequence involving as the key steps (a) the enantioselective synthesis of retronecine and its enantiomer, (b) the enantioselective synthesis of (+) -trachelanthic acid and its enantiomer, and (c) a combination of each segments.Syntheses of all four possible diastereomers of etoposide and its aminoglycosidic analogues have been achieved via optical resolution of (±) -podophyllotoxin by glycosidation with D- and L-sugars.

著者

大村 智

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.58, no.5, pp.392-393, 2000-05-01 (Released:2009-11-13)

参考文献数

5

著者

丸山 透 中井 久郎

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.65, no.5, pp.481-491, 2007-05-01 (Released:2010-10-20)

参考文献数

86

被引用文献数

3 3

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The pathways of prostaglandin (PG) and thromboxane (TX) biosynthesis starting from arachidonic acid are shown in Scheme 1. It is well known that PGs and TX play an important role in maintaining homeostatsis. Since the discovery of these agents, much attention has been paid to their therapeutic potential. Massive efforts have been made to achieve their efficient chemical synthesis because a sufficient supply of these rare local hormones is exclusively dependent on their synthesis. Among the many synthetic methods described in the literature, Corey's and Noyori's are representative ones because both of these approaches are highly efficient and allow the production of all the naturally occurring PGs and a wide range of structural analogues. Discovery of a stereoselective method for the reduction of prochiral 15-ketone was another challenge in relation to the highly efficient synthesis of PGs. In this review, we describe methods for the synthesis of PGs and TX, including stereoselective reduction of 15-ketone.