著者
砂塚 敏明 長光 亨 大村 智
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.54, no.9, pp.740-751, 1996-09-01
参考文献数
48
被引用文献数
3

A total synthesis of the microbial metabolite (+) -lactacystin (1), the first non-protein neurotrophic agent, has been achieved in 11 steps (14% overall yield) from 2 (R), 3 (S) -3-hydroxyleucine. The key steps in the elaboration of the lactam moiety include the stereoselective hydroxymethylation of oxazoline and an asymmetric allylboration of the aldehyde which introduce the hydroxyl and methyl substituents at C (6) and C (7).<BR>This new asymmetric approach furnished four stereoisomers of 3-hydroxyleucine as required starting material in high overall yield and enantiomeric purity.<BR>Furthermore, the construction of several active analogs and the structure-activity relationships of lactacystin are also described.
著者
濱口 浩三
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.11, pp.1052-1060, 1988-11-01 (Released:2009-11-13)
参考文献数
37
被引用文献数
1 1

In this review I first described the stability of proteins obtained from unfolding experiments and how the replacement of a specified amino acid residue with other residues in a protein affects the protein stability. Second, I described the kinetics of unfolding and refolding of proteins. The transition from folded state to unfolded state or from unfolded state to folded state is highly cooperative, and no structural intermediate is detected. Therefore, it is difficult to understand how the regular structure of the native protein is formed from the unfolded molecule. Finally I described the pathway of the disulfide bond formation from reduced proteins.
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

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
溝口 玄樹
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.75, no.3, pp.253-254, 2017
被引用文献数
3

<p>Polyoxygenated steroids cardenolides, typified by ouabagenin, possess a broad spectrum of biological activity such as inotropic activity. Due to their unique structure, including unusual <i>cis</i>-fused A/B- and C/D ring junction, and a number of β-configured oxygenated functional group, they have been an attractive target in chemical synthesis. In this review, recent developments in the practical synthetic strategies toward these cardenolides are described.</p>
著者
冨士 薫 野出 学
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.42, no.3, pp.193-205, 1984-03-01 (Released:2010-01-22)
参考文献数
76
被引用文献数
9 9

A carbon-heteroatom bond has the hard-soft dissymmetry as well as the charge dissymmetry. Thus, a pertinent combination of a hard acid and a soft nucleophile can cleave the carbon-heteroatom bond. This article describes a number of combination systems of a hard Lewis acid and a soft nucleophile which have been developed for the cleavage of C-O, C=C, C-NO2, and C-X bonds.
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

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
刈米 孝夫
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.43, no.8, pp.798-806, 1985-08-01 (Released:2009-11-13)
参考文献数
27

I discussed progressive processing of soap, alkylbenzene, long chain alcohols, α-olefin and synthetic surface active agents connected with foreign situation.Also it is described the changing of inorganic builders, other additives, their formulation and various kinds of continuous sulfation/sulfonation processes by SO3-gas and finally estimated the future trend of synthetic detergent and their related field.
著者
明石 満 赤木 隆美
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.5, pp.520-528, 2004-05-01 (Released:2009-11-13)
参考文献数
44
被引用文献数
1 1

Monodisperse polymeric nanospheres, which consist of hydrophobic core and hydrophilic corona on their surfaces, were prepared by the free radical dispersion copolymerization of hydrophobic monomers and hydrophilic macromonomers in a polar solvent. For example, copolymerization of methacrylate-terminated poly (ethylene glycol) (PEG) macromonomers and styrene in ethanol/water mixture gives water dispersible PEG coated nanospheres with a mean diameter around 100-2000 nm. An electron spectroscopy for chemical analysis (ESCA), dynamic light scattering (DLS) and transmission electron microscopy (TEM) observation of ultrathin cross section embedded in a resin supported accumulation of PEG component at the surface of nanospheres. The core-corona type nanospheres can be widely applied to various technological and biomedical applications, because of their possible variety of chemical structure. These nanospheres were utilized as oral drug carriers for peptide drugs physically adsorbed on the nanosphere surfaces, and demonstrated to be useful carrier for incorporating highly water-soluble peptides. Moreover, lectin-immobilized nanospheres could efficiently capture HIV-1 particles and HIV-1-capturing nanospheres may have great potential as a prophylactic vaccine against HIV-1 infection through sexual intercourse.
著者
橘 和夫
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.45, no.9, pp.898-908, 1987-09-01 (Released:2009-11-13)
参考文献数
48
被引用文献数
1 2

Two classes of shark repellent factors have been isolated, guided by their ichthyotoxicity, from the defense secretions of two species of soles. One class comprises series of steroid monoglycosides, namely, pavoninins from a western Pacific species, Pardachirus pavoninus, and mosesins from the other in the Red Sea known as Moses sole, P. marmoratus. The other class consists of a series of surfactant peptides of 33 amino acid residues, pardaxins. This account deals with structure elucidation of these factors, where emphasis is put on the process from inference of chemical structures by spectroscopic and other customary techniques to their establishment by design of unconventional but firmly corroborative experiments. Diverse bioactivity of these factors is also discussed based on rationale with their amphiphilic structures, which are destined to interact with biological lipid bilayer membranes.
著者
鈴木 教之
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.65, no.4, pp.347-357, 2007-04-01 (Released:2010-10-20)
参考文献数
92
被引用文献数
10 13

It is generally known that small cyclic alkynes such as cyclopentyne is extremely reactive and unstable. Therefore it has been believed impossible to isolate cyclopentyne compounds.We recently reported that low-valent group 4 metallocenes reacted with 1, 2, 3-butatrienes to give 1-metallacyclopent-3-yne complexes and that resulted compounds are surprisingly stable and isolable. We succeeded in determination of their molecular structures by X-ray diffraction analyses, and showed that these are five-membered cyclic alkynes, while π, π-interaction of butatriene was also suggested. In this review, the preparation, structure and reactivity of these 1-metallacyclopent-3-yne compounds are described.The 1-zirconacyclopent-3-yne complexes reacted with another 'zirconocene' to form bimetallic complexes in which the cyclic alkyne coordinated to the other zirconocene moiety, indicating that the zirconacyclopentyne behaved as an alkyne. Seven-membered cyclic alkynes were also prepared from 1, 2, 3-butatriene and a zirconocene-alkyne compound. Protonolysis and subsequent nucleophilic attack to aldehyde gave allenyl or dienyl alcohol depending on proton source.
著者
若宮 淳志
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.1304-1305, 2006-12-01 (Released:2010-10-20)
参考文献数
10
被引用文献数
1

This mini review focuses on the developments of Ir-catalyzed direct borylation of arenes via C-H activation. The regioselectivity of the borylation is mainly controlled by the steric factors. The regioselective C-H bond activation/functionalization can provide the borylated arenes which are otherwise difficult to synthesize. Recent applications of the borylation to polycyclic aromatic hydrocarbons and porphyrins are briefly described.
著者
久枝 良雄 嶌越 恒
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.63, no.8, pp.780-790, 2005-08-01 (Released:2009-11-13)
参考文献数
27
被引用文献数
3 3

Vitamin B12-dependent enzymes, involving the cobalt species as a catalytic center, mediate various molecular transformations in vivo. In order to use vitamin B12 derivatives (cobalamins) as green catalysts, various studies have been carried out such as a chemical modification of cobalamin or the fixation of B12 derivative on electrodes.The Co (I) species of vitamin B12 derivative is widely known as a supernucleophile that forms an alkylated complex by reaction with an alkyl halide. Such reaction is efficient for dehalogenation of various organic halides. Therefore, vitamin B12 derivatives can be used as catalysts for reductive degradation of organic pollutant such as DDT. In addition, the alkylated complex is a useful reagent for forming radical species as the cobalt-carbon bond is readily cleaved homolytically by photolysis or electrolysis. Therefore, the application of the alkylated complex to organic synthesis is quite interesting from the viewpoint of a radical-forming reagent. This review article summarizes recent progress in homogeneous and heterogeneous catalytic reactions mediated by vitamin B12 derivatives.
著者
吉川 彰一 野村 正勝 森田 幸男
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.34, no.1, pp.36-40, 1976-01-01 (Released:2009-11-13)
参考文献数
14
被引用文献数
3 3

ベンゼンとアセトニトリルとの高周波放電反応を行った。液体窒素トラップからえた液状成分の分析からアセトニトリルやベンゼンの単独放電反応でえられる特徴的な生成物の他にベンゾニトリル.ベンジルシアニド, o, m, p-トルニトリルやo, m, p-ジシアノベンゼンが生成していることを認めた。アセトニトリルの単独放電反応ではプロピオニトリル, ブチロニトリル, クロトニトリル, マロノニトリル, スクシノニトリル, グルタロニトリルなどが生成し, この他にテトラシアノエチレンが生成しているのが放電反応物のESRスペクトルから推定された。PBNをラジカル補捉剤として使用したベンゼンの高周波放電反応における活性種のトラップ実験ではベンジルラジカルが生成しているのがESRスペクトルから推定された。