著者

実吉 峯郎

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.40, no.2, pp.136-146, 1982-02-01 (Released:2009-11-13)

参考文献数

102

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The synthesis and biological activities of 1-β-D-arabinofuranosylcytosine (Ara C) and related compounds are reviewed and discussed under following headings : 1. Synthesis of 1-β-D-arabinofuranosylcytosine. 1-1 synthesis from uridine ; 1-2 synthesis from cytidine ; 1-3 synthesis via coupling of bases with suitably protected sugars ; 1-4 synthesis via D-arabinose oxazoline derivative. 2. Biological activities of 1-β-D-arabinofuranosylcytosine and related compounds. 2-1 antitumor and antiviral activities ; 2-2 biological activation of 1-β-D-arabionfuranosylcytosine in vivo and its mode of biological actions ; 2-3 inhibition of DNA polymerases by Ara CTP 2-4 other arabinofuranosyl nucleosides. 3. Some derivatives of 1-β-D-arabinofuranosylcytosine. 3-1 modifications on cytosine moieties; 3-2 sugar-modified derivatives; 3-3 depot form of Ara C and Ara CMP. 4. Scope and limitation of cancer chemotherapy using 1-β-D-arabinofuranosylcytosine and related compounds are also finally discussed.

著者

浜田 翔平

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.8, pp.813-815, 2020-08-01 (Released:2020-08-06)

参考文献数

10

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DNA encoded library (DEL) has emerged as a widely utilized chemical library, possessing DNA-tag on each compound, for discovering hit compounds in drug discovery. However, synthetic methods for DEL are not fully exploited due to the difficulty in chemical transformation of DNA encoded compounds. This mini-review focuses on the recent development on organic synthesis for diversity expansion of DEL.

著者

大石 武 中田 忠

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.39, no.7, pp.633-641, 1981-07-01 (Released:2009-11-13)

参考文献数

30

被引用文献数

3 4

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Highly stereocontrolled reduction of α-methyl β-keto esters, 3-hydroxy-2-methyl ketones, and α, β-epoxy ketones with Zn(BH4)2 has been described. In every case, the predominated products were found to be erythro-alcohols. A plausible mechanism to account for these high selectivity is discussed.Synthetic studies of erythronolide A starting from erythro-3-hydroxy-2-methylpropionates prepared by the reduction of the corresponding β-keto esters with Zn(BH4)2 have also been described.

著者

佐々木 正

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.39, no.4, pp.289-300, 1981-04-01 (Released:2009-11-13)

参考文献数

91

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Beginning from a general survey of the characters of polycarbocyclic compounds as one of the possible future ones, the importance and utility of the pericyclic reactions are discussed from a viewpoint of their synthesis and their synthesis is reviewed on the focus of the intramolecular Diels-Alder reactions.

著者

高久 洋

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.39, no.2, pp.109-121, 1981-02-01 (Released:2009-11-13)

参考文献数

108

被引用文献数

1

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8-Oxyquinolyl group has been widely applied to the synthesis of oligonucleotides.

著者

加藤 南

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.185-186, 2019-02-01 (Released:2019-02-08)

参考文献数

8

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Two dimensional Covalent Organic Frameworks (2D COFs) are new porous materials synthesized from only organic molecules. The 2D COFs consist of light elements that can form strong covalent bonds. The properties of 2D COFs such as pore size, shape and character are easily controlled. The 2D COFs are expected to be applied for a gas storage, an electrochemical device and so on. This review summarized the characteristics and new synthetic methods of 2D COFs.

著者

山田 俊一

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.11, pp.1083-1096, 1970-11-01 (Released:2009-11-16)

参考文献数

105

被引用文献数

7 6

著者

山内 泰宏 星本 陽一 生越 專介

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.79, no.7, pp.632-641, 2021-07-01 (Released:2021-07-07)

参考文献数

72

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Practical methods have been established for the synthesis of multifunctional N-heterocyclic carbenes (NHCs) via the introduction of substituents on either the nitrogen atom(s) or the backbone of the NHCs. However, their use has been mainly limited to acting as multidentate ligands for metal complexes. Herein, results of our recent studies on the synthesis and application of N-phosphine oxide-substituted imidazolylidenes (PoxIms) as novel type of multifunctional NHCs are discussed. PoxIms were used not only as a mono-/bi-dentate ligand for mono-/bi-metallic complexes, but also as an external stimuli-responsive Lewis base for achievement of the frustration revival strategy as well as a reagent for the direct phosphinoylation of CO2 and carbonyl compounds. These results manifest the pioneering role of PoxIms as a multifunctional multipurpose NHC.

著者

松尾 貴史

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.79, no.4, pp.311-321, 2021-04-01 (Released:2021-04-07)

参考文献数

49

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Hoveyda-Grubbs-type complexes with a ruthenium center coordinated by an N-heterocyclic carbene (NHC) and a 2-alkoxybenzylidene ligands have gained increased applicative importance as catalysts for olefin metathesis because the complexes have suitable reactivities and stabilities in a wide range of reaction media. Furthermore, this type of catalysts has also been applied for biochemical research projects including the construction of artificial biocatalysts and the regulation of in-cell bioreactions because the ruthenium-olefin interaction, a driving force of olefin metathesis mediated by Hoveyda-Grubbs-type complexes, provides the specificity among functional groups in biomolecules. In this context, we have investigated the structural modification of Hoveyda-Grubbs-type complexes aiming at the application of the complexes to biomolecules. In parallel, we have also studied the mechanism of olefin metathesis in aqueous media. In this article, we firstly describe the construction of an artificial metalloenzyme with olefin metathesis activity using α-chymotrypsin. The artificial metalloenzyme displayed the substrate specificity with the protein surface charge state. Next, we demonstrate the importance of chloride anion in solutions to attain efficient olefin metathesis reactions in aqueous media and the reactivity control of Hoveyda-Grubbs-type complexes through second-coordination sphere effect. Finally, we introduce the ruthenium complex transfer reaction between Hoveyda-Grubbs-type complexes and biomolecules (peptides and proteins) through the ruthenium-olefin specific interaction. The reaction potentially serves a new type of chemical modification strategy toward biomolecules.

著者

時任 宣博

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.52, no.2, pp.136-148, 1994-02-01 (Released:2010-01-28)

参考文献数

39

被引用文献数

4 9

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Recent studies on the synthesis, structure, and reactivity of kinetically stabilized double-bond compounds between group 14 metals (M=Si, Ge, and Sn) and heavier chalcogens such as sulfur or selenium are reviewed. Three different approaches for the formation of “heavy ketones” were examined, i. e., (i) the thermal retrocycloaddition of 1, 2, 4, 3-trichalcogenametallolanes bearing a new steric protection group, 2, 4, 6-tris- [bis (trimethylsilyl) methyl] phenyl (denoted as Tb), (ii) the reactions of kinetically stabilized divalent group 14 metal species, Tb (Ar) M, with an epichalcogenide or elemental chalcogen, and (iii) the dechalcogenation reactions of 1, 2, 3, 4, 5-tetrachalcogenametallolanes, Tb (Ar) MY4 (Y=, S, Se). As a result of kinetic stabilization by the combination of Tb and 2, 4, 6- triisopropylphenyl (Tip) group, silanethione Tb (Tip) Si S and germanethione Tb (Tip) Ge=S were successfully isolated as monomeric and stable crystalline compounds, while the corresponding stannanethione Tb (Tip) Sn = S was synthesized as a monomeric species stable in solution, Of particular note is the X-ray crystallographic structure analysis of germanethione, which revealed the completely trigonal planar geometry for the germathiocarbonyl unit and the remarkable bond shortening for the Ge-S double bond.

著者

山田 祥一郎

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.27, no.10, pp.939-950, 1969 (Released:2009-11-13)

参考文献数

76

著者

中村 斐有 安井 孝介 Phil S. Baran

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.4, pp.333-343, 2021-04-01 (Released:2021-04-07)

参考文献数

32

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Teleocidine B family was isolated in1960 by Sakai group and was shown to have highly potent protein kinase-C (PKC) activation, similar to that of phorbol and related natural products. In this report, we have developed a unified total synthesis of teleocidins B-1-B-4 in 11 chemical steps. The highlights of the work are 1) the Ni catalyzed electrochemical amination, 2) Cu-mediated aziridine opening followed by direct macrolactamization, and 3) the tactical combination of C-H borylation and a redox-relay chain walking (RRCW) methodology to make the carbon quaternary center.

著者

小西 彬仁 安田 誠

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.3, pp.224-233, 2021-03-01 (Released:2021-03-10)

参考文献数

46

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Nonalternant hydrocarbons, which involve odd-membered rings, are an intriguing family for investigations of the structure-property relationship of π-conjugated carbocycles. Bicyclic nonalternant hydrocarbons, azulene, pentalene and heptalene, are the most fundamental molecules in a series of nonalternant hydrocarbons. Over the last 15 years, the chemistry of nonalternant hydrocarbons has experienced a remarkable renaissance mainly thanks to advances in synthetic methodologies. Ring-annulated nonalternant π-systems, in which some benzenoid rings are attached into the nonalternant frameworks, are the key players in their resurgence. The ring annulation impacts the electronic structures of nonalternant subunits, which modulates the HOMO-LUMO gap and creates perturbations in their inherent (anti)aromatic nature. The tunable, narrow HOMO-LUMO gap has offered rich studies into the electronic properties of open-shell characters and into their potential applications as functional organic optoelectronic materials. This article describes our recent studies on the synthesis and characterization of π-extended nonalternant hydrocarbons, containing azulene, pentalene and heptalene frameworks.

著者

長澤 和夫

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.43-53, 2021-01-01 (Released:2021-01-09)

参考文献数

31

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This review deals with our synthetic efforts for guanidine alkaloid of saxitoxin (STX), a paralytic shellfish toxin. STX shows potent inhibitory activity against voltage-gated sodium channels (NaVs), which are membrane proteins that involve in the generation and propagation of action potentials in neurons. More than 50 analogs of STX have been isolated from nature, and these analogs commonly possess characteristic tricyclic core skeleton including two kinds of 5-memberd and 6-memberd cyclic guanidine. For the synthesis of the core structure, we have developed a neighboring acyl group assisted cyclization strategy to give tricycle with a fully protected form of saxitoxinol under quite mild conditions. This key intermediate allows us total synthesis of (+)-decarbamoyl saxitoxin (dcSTX), (+)-gonyautoxin 3 (GTX3) including and STX. Besides, we have achieved the synthesis of 11-saxitoxinethanoic acid (SEA), which is an unusual STX derivative bearing carbon-carbon bond at the C11 position by applying Mukaiyama aldol condensation reaction with silyl enolether derived from the key intermediate of fully protected saxitoxinol. NaV inhibitory activities of some synthetic derivatives with C11-substituents in STX were also described.

著者

魚住 泰広 森 美和子 柴崎 正勝

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.49, no.10, pp.937-946, 1991 (Released:2009-11-16)

参考文献数

35

被引用文献数

1 2

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Molecular nitrogen was incorporated into organic compounds via titanium nitrogen complex [TiNMg2Cl2·THF]. Namely, the reaction of titanium isocyanate complex [3THF· Mg2Cl2OTiNCO] prepared from titanium nitrogen complex [TiNMg2Cl2·THF] and CO2 with acid anhydrides afforded cyclic imides and quinazoline derivatives. Using the combination system of nitrogenation and palladium catalyzed carbonylation, phthalimide, isoindolinone, and quinazolines were synthesized from an aryl halide. Furthermore, coupling reaction of ketones with an aryl or vinyl halides in the presence of Pd (0) and titanium isocyanate complexes smoothly proceeded to give divinyl amines or arylvinyl amine via transmetalation.

著者

中尾 英雄 柳沢 宏明 杉村 征夫 平岡 哲夫

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.35, no.7, pp.563-574, 1977-07-01 (Released:2009-11-13)

参考文献数

36

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Synthetic studies on 7-methoxycephalosporins are reviewed under the following subjects : 1. synthesis of cephamycin derivatives 2. chemical methoxylation a) direct methods b) indirect methods 3. author's work a) synthesis by oxidation of novel Schiff bases b) synthesis from 7-haloacetamidocephalosporins 4. synthesis of new antibacterial derivatives.

著者

西郷 和彦

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.1240-1250, 2006-12-01 (Released:2010-10-20)

参考文献数

19

被引用文献数

5 5

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We carried out systematic studies on the preferential and diastereomeric crystallizations with the aid of X-ray crystallographic analyses and found that there is high correlation in molecular length between a target racemate and a derivatizing/resolving agent. On the basis of the results, we proposed relative molecular length and CH/π rules. The rules were applied to the development of non-natural enantiopure compounds, which were highly useful in asymmetric syntheses, chiral polyamide synthesis, and so on. Recent results concerned with the enantioseparation by phosphonothioic and phosphinothioic acids and with the asymmetric synthesis of phosphorothioates are also described.

著者

岡本 佳男 海田 由里子

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.51, no.1, pp.41-53, 1993-01-01 (Released:2009-11-16)

参考文献数

131

被引用文献数

12 15

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Polysaccharides such as cellulose and amylose are the most accessible optically active polymers. The polysaccharides themselves show rather low chiral recognition, but their derivatives show high chiral recognition and afford useful chiral stationary phases (CSPs) for HPLC. In this review, optical resolution by cellulose esters, especially benzoates, and by various phenylcarbamates of cellulose and amylose is discussed. Chiral recognition abilities of aralkylcarbamates of cellulose and amylose are also evaluated.

著者

川合 恭平 鈴木 汎

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.6, pp.494-500, 1979-06-01 (Released:2009-11-13)

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We, Toagosei Chemical Industry, have buckled down seriously to the safety problem with making the best use of our experience of plant accidents happened in the past.With an explosion accident in 1952 as a momentum, our plant operation was standardized. Then, with an explosion accident in 1972 as a momentum, an expert committee for the prevention of plant accidents was institutionalized.By the said committee, the checking for causes of accidents is done as to each stage of research, engineering, and test operation. The check list is used for this purpose. Now, we would introduce the part relating to the explosion.Differential Scanning Calorimeter is effective for the checking against explosive chemicals of which counterplan is difficult to be set.

著者

宗行 龍之祐 谷田 博

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.36, no.6, pp.454-466, 1978-06-01 (Released:2010-01-22)

参考文献数

88

被引用文献数

1 2

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In relation to Friedel-Crafts acylation, complexes of (ArH·MX3), (ArH·HX·MX3), and (RCOX·MX3) were chronologically reviewed on their structual formulations up to date. Properties of their complexes and their roles in the reaction were explained in terms of their differences between π-and σ-type structure. The X-ray crystal analytical results were quoted to make clear the structual small changes between π-axial and π-edgewize complexes and between ionic and nonionic complexes of (RCOX·MX3), and also to demonstrate the characteristics of σ-complex. From the recent results obtained in nonconventional attack at ipso position, some comment was added about the difficulty of finding structual relationship between intermediate complexes and products.