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

---

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

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

---

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

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

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

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

---

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

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

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.

著者

野上 寿 松田 紀雄

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.13, no.11, pp.526-532, 1955 (Released:2010-10-20)

参考文献数

42

著者

海野 雅史 松本 英之

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.62, no.2, pp.107-115, 2004-02-01 (Released:2009-11-13)

参考文献数

36

被引用文献数

2 4

---

Octasilacubane is an intriguing polyhedral polysilane because of its unique electronic properties arising from highly strained Si-Si σ-bonded framework. The first octasilacubane, octakis (t-butyldimethylsilyl) octasilacubane was reported by our group in 1988, as the first example of Platonic solid compounds comprising Group 14 elements other than carbon. We then prepared the alkyl-substituted one (ThexSi)8 (Thex = 1, 1, 2-trimethylpropyl) in 1992. These octasilacubanes are fairly stable, and various reactions, e.g., halogenation, oxidation, and photoreaction have been reported. Thus, the reaction of (ThexSi)8 with PCl5 leading to dichlorides via skeletal, rearrangement, the halogenation with Br2 or I2 leading to dibromides or diiodides, and the reductive dehalogenation of these dihalides with sodium to regenerate (ThexSi)8. Photo-initiated partial oxidation with DMSO gave monooxaoctasilahomocubane and dioxaoctasilabishomocubane. In this paper, in addition to these reactions, structure, thermal property, photoluminescent property, and UV property of octasilacubanes were summarized.

著者

広田 穣

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.23, no.2, pp.99-116, 1965-02-01 (Released:2011-07-05)

参考文献数

141

被引用文献数

1 1

著者

赤堀 四郎 泉 美治

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.14, no.6, pp.367-378, 1956 (Released:2010-10-20)

参考文献数

72

被引用文献数

1

著者

皆川 源信

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.31, no.5, pp.420-426, 1973-05-01 (Released:2009-11-13)

参考文献数

47

被引用文献数

1 2

著者

稲本 直樹 秋葉 欣哉 山田 紘一

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.28, no.2, pp.105-128, 1970-02-01 (Released:2010-01-28)

参考文献数

166

被引用文献数

1 1

著者

山中 龍雄

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.14, no.3, pp.125-136, 1956-03-01 (Released:2010-10-20)

参考文献数

122

著者

納谷 洋子

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.46, no.5, pp.447-454, 1988-05-01 (Released:2010-01-22)

参考文献数

18

被引用文献数

1

---

The presence of a molt-inhibiting hormone (MIH) in crustaceans versus the molting hormone (ecdysteroids) has been biologically demonstrated, however, only a little of the chemical nature of MIH is known so far Our attempt to isolate MIH produced in the X-organ of the eyestalks (ES) resulted in the characterization of xanthurenic acid as an ecdysone biosynthesis inhibitor (EBI) In addition, it was found that 3-hydroxy-L-kynurenine (3-OH-K) present in the X-organ of ES was also biotransformed into xanthurenic acid. The inhibitory action was shown in the cultured Y-organ-complex homogenate as well as in the crayfish by injection of 3-OH-K that revealed the delay of ecdysis. The preliminary study of ED50 of the active compounds appeared to account for most of but not the full potency of ES extract. Therefore, a molt-inhibiting phenomena is probably the result of the action by the multiple factors including EBI. After the mode of inhibitory action of the recently isolated sinusgland neuropeptide is shown, the involvement of a hormone in the negative control of molting will be clarified.

著者

Yohsuke Yamamoto Kin-ya Akiba

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.62, no.11, pp.1128-1137, 2004-11-01 (Released:2009-11-13)

参考文献数

31

被引用文献数

15 21

---

Various carbon and boron compounds bearing a 1, 8-disubstituted anthracene skeleton were synthesized and characterized by X-ray analysis. They showed three types of structures based on the kinds of substituents. The first one is symmetrical and is a loose pentacoordinate structure, which has the sp2 carbon or boron atom and the two weak apical interactions. The next one is an unsymmetrical tetracoordinate structure, which has the sp3 central atom. The last one is symmetrical and is a tight pentacoordinate structure, which resulted from the special feature of the fluorine substituents on the boron. The existence of hypervalent interaction was proved by the Atoms In Molecules Theory, experimental electron distribution analysis and a comparison among the structures of tight and loose pentacoordinate species. The synthesis and structures of hypervalent carbon compounds with a 2, 6-bis (aryloxymethyl) benzene ligand are also discussed.

著者

岡本 佳男 八島 栄次

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.8, pp.792-804, 1987-08-01 (Released:2010-01-22)

参考文献数

68

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Three different types of asymmetric polymerizaitons of methacrylates have been achieved successfully. Racemic α-substituted benzyl methacrylates were polymerized with a high enantiomer-selectivity over 90% in the polymerization by (-) -sparteine-Grignard reagent complexes. Optically active polymethacrylates with nearly 100% one-handed helicity were obtained in the polymerization of such bulky esters as triphenylmethyl methacrylate with chiral anionic initiators. These chiral polymers were found to be very effective in separating the optical isomers under HPLC conditions. A very high enantiomer selection by the growing chain end with a stable helical structure was also attained in the polymerization of a bulky racemic monomer phenyl-2-pyridyl-ο-tolylmethyl methacrylate.

著者

小方 芳郎 木村 眞

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.7, pp.581-594, 1979-07-01 (Released:2009-11-13)

参考文献数

85

被引用文献数

3 8

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Metal hypohalites (e. g. NaOCl) can be used not only for selective oxidation and halogenation of organic compounds, but also for oxidative removal of pollutants such as aromatic compounds and surfactants, especially nitrogen compounds which results in the eutrophication of sees and lakes.The present article reviews the properties and oxidative preparation, reactions of hydrocarbons (aliphatic and aromatic), alcohols, aldehydes, ketones, ethers, carboxylic acids, ammonia, amines, amides (including urea), and sulfur compounds (including sulfonic acids) with the hypohalites. On UV irradiation hypohalites delivers atomic oxygen and HO·which are highly active oxidants, thus initiate a chain reaction by abstracting hydrogen atom, and can be used for removal of pollutants. The review emphasizes the mechanisms for hypohalite oxidation and photo-oxidation of compounds polluting waste water.

著者

早川 勇夫 藤原 敏洋 江幡 勉

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.54, no.1, pp.62-67, 1996-01-01 (Released:2009-11-16)

参考文献数

13

被引用文献数

3 5