著者

佐藤 恒夫 安孫子 淳 正宗 悟

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.44, no.4, pp.309-325, 1986-04-01 (Released:2010-01-22)

参考文献数

46

被引用文献数

2 5

---

This account examines double asymmetric induction from theoretical and practical viewpoints. In the context of four major organic reactions-the aldol, Diels-Alder, catalytic hydrogenation, and epoxidation-it is shown that a double asymmetric induction can be analyzed in terms of the single asymmetric reactions of each of the two chiral reactants. A rule which qualitatively relates the results of these single asymmetric reactions with the outcome of the double asymmetric reaction is proposed. A powerful new strategy based on this rule for the predictable creation of new chiral centers is discussed and the use of this strategy for the synthesis of sugars and macrolides is presented.

著者

安孫子 淳

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.7, pp.564-573, 1996-07-01 (Released:2010-01-28)

参考文献数

28

被引用文献数

2 3

---

New chiral auxiliaries based on the isoxazolidine skeleton have been developed. Characteristic feature of these auxiliaries are : 1) High reactivity for asymmetric alkylations. 2) Acylation of the auxiliary with an acid chloride and an amine, or DCC condensation. 3) One step transformation of the reaction products to the corresponding chiral alcohols, aldehydes and ketones without loss of the stereochemical integrity with the recovery of the auxiliary. Asymmetric alkylation of chiral β-substituted alkanols via their triflates lead to the easy access to the “reduced polypropionate units” as well as the first synthesis of the marine natural product (+) -siphonarienone. Enantiomerically pure axially dissymmetric cyclohexylidene compounds were synthesized using asymmetric Horner-Emmons reaction of the phosphonate derived from the auxilliary.

著者

酒井 浄 中村 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.36, no.2, pp.93-106, 1978-02-01 (Released:2009-11-13)

参考文献数

91

被引用文献数

2 2

---

Advances in Prostaglandin (PG) fields after the discovery of PGG2 and PGH2 are reviewed. Biological activities of PGG2, H2, I2 and TXA2 are briefly explained, and the synthetic studies on these new PGs reviewed. Improvements in the synthesis of primary PGs are also summarized.

著者

酒井 浄 末宗 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.46, no.4, pp.334-343, 1988-04-01 (Released:2009-11-13)

参考文献数

48

被引用文献数

1 1

---

Starting with (+) - and (-) -limonenes as chiral synthons, syntheses of biologically active compounds such as prostaglandins, (+) -brefeldin A and nepetalactones have been studied. The key-step of these conversions is based on the stereoselective cyclization of 3, 4-disubstituted 4-pentenals into cis-3, 4-disubstituted cyclopentanones using the Rh (I) -complex.Ring cleavage and reconstruction of five and six membered rings under acetalization conditions are also discussed.

著者

周東 智 市川 聡 阿部 洋 松田 彰

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.66, no.1, pp.50-60, 2008-01-01 (Released:2010-06-28)

参考文献数

22

被引用文献数

2 4

---

Despite considerable progress and extensive effort, a general method for highly stereoselective glycosylation particularly for the 1, 2-cis-glycosylation has not yet been developed and therefore is required. The α/β-stereoselectivity in glycosylation can be affected by the steric and stereoelectronic (anomeric) effects around the anomeric center, which depend on the conformation of the glycosyl donor substrates. Therefore, we hypothesized that highly α- and β-selective glycosylation can be realized by employing conformationally restricted substrates. We showed that the α/β-stereoselectivity was significantly increased by the conformational restriction and was completely inverted by changing the substrate conformation from the 4C1-form into the 1C4-form in radical and nucleophilic C-glycosylation reactions as well as in O-glycosylation reactions. The conformational restriction of substrates also effectively facilitates the α- and β-selective radical cyclization reaction at the anomeric position. Using the method, C-glucoside trisphosphates designed as Ca2+-mobilizing agents were successfully synthesized.

著者

津江 広人 堀口 雅弘 田村 類 藤井 孝太郎 植草 秀裕

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.12, pp.1203-1212, 2007-12-01 (Released:2010-10-20)

参考文献数

88

被引用文献数

35 52

---

A single crystal X-ray diffraction method is the most powerful technique for the crystal structure determination of both organic and inorganic compounds. However, a number of organic compounds crystallize in a form of polycrystalline powder rather than a single crystal of suitable size and quality for X-ray crystallographic analysis. Recent remarkable developments of both software and hardware have turned X-ray powder diffraction method into another significant technique for solving crystal structure. In fact, not a few crystal structures solved from the powder diffraction data of organic compounds have been published in scientific papers. At the same time, however, it is also true that crystal structure solution from powder data is still a challenging subject; indeed, the structure solution cannot be executed in such an automatic manner as established in the single crystal method. In this article, we describe the details of the structure solution processes from X-ray powder diffraction data, together with the experimental know-how gained from our experiences.

著者

松本 和男 関 雅彦

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.49, no.1, pp.26-41, 1991-01-01 (Released:2010-01-28)

参考文献数

68

被引用文献数

6 9

---

This review deals with the chemistry of aspartic acid derivatives and its utilization for drug-syntheses. It should be noted in particular that “Aspartylation”, in which the aspartic acid skeleton is introduced into the target molecules by the use of various aspartic acid synthons, provides a useful methodology for the prepara-tion of the pharmaceuticals.

著者

市村 通朗

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.5, pp.548-558, 2006-05-01 (Released:2010-10-20)

参考文献数

33

被引用文献数

1 2

---

The microbial screening is an approach for discovering medicines out of microbial metabolites. The natural products (microbial metabolites) are known to possess very unique and complicated structure that could not be imagined. In addition, many of them also have highly potent and selective (specific) biological activities. This report focuses on the feature and present situation of microbial screening in drug discovery field. Firstly, the recent study and development on antitumor antibiotics, duocarmyicins (related compounds) and calicheamicin γ1IIthat indicate extraordinary potent activity, are reviewed. Next, the biochemical and pharmacological study on KS-505a (C 40 tetraterpenoid) produced by Streptomyces argenteolus, a PDE 1 (calcium/calmodulin-dependent phosphodiesterase) isoform selective inhibitor, is presented. The relationship between the microbial screening and recent “chemical biology” or “chemical genetics” approach is also discussed, using for examples, the mode of action of rapamycin and stem cell-based medicine. Finally, the basic strategy in microbial screening (method, target diseases etc.) is described.

著者

衣川 雅彦 新井 仁 小笠 剛裕 河西 政次

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.57, no.5, pp.401-406, 1999-05-01 (Released:2009-11-16)

参考文献数

16

被引用文献数

2 5

---

A convenient large-scale preparation of the indoloquinone antitumor agent EO9 has been developed. A Nenitzescu reaction has been used to prepare the indole skeleton having all functional groups necessary for its conversion into a key intermediate in a short synthesis of the indoloquinone EO9. Moreover, the hazardous reagent, Fremy's salt was replaced by safer one, [bis (trifluoroacetoxy) iodo] benzene, for oxidation of the 4-aminoindole to the corresponding indoloquinone, and high quality EO9 was easily obtained by choosing acetonitrile as the solvent in the substitution reaction of the methoxy group with ethylenimine to introduce the aziridinyl group into the precursor.

著者

山田 昌樹 大水 博

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.60, no.5, pp.512-513, 2002-05-01 (Released:2009-11-13)

参考文献数

3

著者

藤沢 有 宇梶 裕

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.3, pp.186-199, 1989-03-01 (Released:2010-01-22)

参考文献数

93

被引用文献数

12 12

---

The ever advancing development of chemical reactions has initiated enormous progress towards the stereoselective reactions. In almost cases, however, only one isomer of the possible two isomers can be obtained by these reactions and nowadays selective synthesis of both isomers is required. The present article reviews the current advancement for selective diastereoface differentiating reactions to give both isomers especially relating to nucleophilic addition reactions to carbonyl compounds with an asymmetric center. Fundamental significance is to utilize metal reagents possessing various coordinating abilities.

著者

大西 智之

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.59, no.5, pp.448-449, 2001-05-01 (Released:2009-11-13)

参考文献数

2

著者

辻 尚志

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.58, no.7, pp.683-690, 2000-07-01 (Released:2009-11-13)

参考文献数

25

被引用文献数

1 2

---

A series of conformationally constrained nucleoside analogues with two hydroxymethyl groups mimicking the 3'- and 5'-hydroxyl groups of the 2'-deoxyribose were prepared and evaluated for their antiherpetic activity. Among those, 9- [[cis-1'-, 2'-bis (hydroxylmethyl) cycloprop-1'-yl] methy] guanine showed extremely potent antiviral activity against HSV-1. One of the enantiomers with (1'S), (2'R) -configuration (A-5021) was proved to be the active form. A-5021 was more active than acyclovir (ACV) against HSV-1, HSV-2, VZV, HCMV and showed superior activity over ACV in animal models. An efficient process for preparation of A-5021 including enantioselective hydrolysis of the intermediate is described. An oral prodrug AV-038 and anti-VZV drug AV-100 are also described.

著者

新開 一朗

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.432-434, 2000-05-01 (Released:2009-11-13)

著者

吉本 昌文 岩野 雄次 石田 登 平岡 哲夫 岸田 有吉

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.2, pp.176, 1973-02-01 (Released:2009-11-13)

参考文献数

5

著者

佐藤 文憲

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.53, no.4, pp.284-297, 1995-04-01 (Released:2009-11-16)

参考文献数

37

被引用文献数

1 4

---

Brevetoxins are powerful neurotoxins produced by dinoflagellate strain Gymnodinium berve Davis, isolated from the Florida “red tide” dinoflagellate. Their unique structure presents an opportunistic and formidable synthetic problem, particularly with regard to the construction of its medium-sized ring systems. This would almost certainly require new synthetic technology and a carefully designed strategy before yielding to total synthesis. This review deals with some new, practical and efficient synthetic technologies for the construction and chemical manipulation of medium-sized cyclic ether developed in K K.C. Nicolaou's laboratories.First total synthesis of hemibrevetoxin B (3) performed by these technologies is also delineated.

著者

小夫家 芳明

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.30, no.12, pp.992-1005, 1972-12-01 (Released:2010-01-22)

参考文献数

75

被引用文献数

2 3

著者

杉江 敦司

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.4, pp.429-430, 2014

被引用文献数

2

---

Gold nanoparticle whose surface is protected by adsorption of thiols attracts considerable attention as advanced materials. Organic-bond forming reaction on the surface of thiol-capped gold nanoparticle would be effective protocol for introduction of functionality onto gold nanoparticle. This review highlights selected examples of recent advance in organic-reaction inspired surface modification of gold nanoparticle.

著者

野平 博之

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.50, no.1, pp.14-23, 1992-01-01 (Released:2009-11-16)

参考文献数

35

被引用文献数

2 4

---

Some new methods and practical strategies for the efficient resolution of a wide variety of organic componds by means of such crystallization procedures as preferential crystallization, diastereomeric salt formation and their combination are described. Utilizing the organic compounds with high optical purities thus obtained, application study in the following field has been performed;1) verification of the Brewster's theory of optical activity, 2) syntheses of pharmaceutical, agricultural and perfuming chemicals, 3) preparation of optical purity determining agents, 4) preparation of atropisomeric bis (triarylphosphine) as a catalyst for asymmetric hydrogenation, 5) syntheses of ferroelectric liquid crystals. In this article, an outline of our investigation in the above mentioned fields is also described.

著者

篠原 好幸

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.35, no.2, pp.138-146, 1977-02-01 (Released:2009-11-13)

参考文献数

40

被引用文献数

1 2

---

フェノールは合成樹脂, 合成繊維, 農医薬, 界面活性剤等の原料中間体として有機化学工業における重要な基礎物質の一つである。現在全世界で約300万トン以上使用されている。フェノールはF.F.Rungeによって1834年コールタール中より発見され, Karbolsäaure (石炭酸) と命名された。19世紀後半における有機化学工業の発達にともない, フェノールはコールタール中のタール酸より分留により工業的に製造されるようになった。フェノール誘導体の伸張はタール分留のみによる供給に不足をきたし, 合成法が研究され, ベンゼンスルフォン化法 (硫酸法) が1890年代にドイツで企業化された。フェノールは軍用火薬ピクリン酸の原料としても大量使用され, 第1次, 第2次大戦において合成フェノール工業は急速に拡張され, 硫酸法の改良, 塩素化法の企業化等の技術的な発達を促した。第2次大戦中アメリカで発達した石油化学工業はフェノール合成法にも原料, 技術の面で大幅な進展を遂げ, ラッシヒ法の工業化, クメン法の発見, 工業化技術の完成, トルエン法の企業化と目覚ましい展開を見るに至った。現在全世界のフェノールは90%以上が合成法により供給され, コークス炉ガス, コールタール, 石油よりの回収いわゆる天然フェノールは10%以下である。また合成法の80%はクメン法によって生産されている。本稿はフェノール合成法の概略について歴史的に振り返り, 技術的経済的問題についても述べたい。