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.61, no.1, pp.24-34, 2003-01-01 (Released:2009-11-13)

参考文献数

14

被引用文献数

2 5

---

Boron-mediated aldol reaction of carboxylic esters is described in detail. Contrary to the gener-al belief that carboxylic esters are inert toward the conventional enolization conditions, propionate esters are shqwn to have adequate reactivity on the boron-mediated aldol reaction. More impor-tantly, the stereochemical course of the aldol reaction can be controlled by the judicious choice of the enolization reagents. Complementary anti- and syn-selective asymmetric aldol reaction of structurally related chiral esters are developed. Also, novel double aldol reaction is discovered with acetate esters, which provides a precursor to the synthesis of chiral triols of C3-symmetry. Extensive NMR experiments lead to characterize the first carbon-bound boron enolates and the novel doubly borylate enolates as intermediates of the double aldol reaction. A plausible mecha-nism of the double aldol reaction is proposed.

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.5, pp.384-404, 1986-05-01 (Released:2010-04-23)

参考文献数

89

被引用文献数

2 2

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

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

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

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

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

高橋 一公 伊達 隆文 山田 和俊 飯田 弘忠

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.29, no.3, pp.293-297, 1971

被引用文献数

1

---

A prolonged treatment of <I>p</I>-nitrotoluene and benzaldehyde with a sodium-hexamethylphosphoric triamide (HMPA) -benzene mixture was found to give 1-phenyl-2- (4-nitrophenyl) -ethan-1-ol (1) selectively. It was also found that the yield of (1) is sensitively affected by various factors, such as the temperature, the concentration of HMPA, and the reaction time. It may be concluded from the correlation of the yield of (1) and the conversion ratio of <I>p</I>-nitrotoluene that the formation of (1) results from the nucleophilic attack of the <I>p</I>-nitrobenzyl anion, derived from <I>p</I>-nitrotoluene, on the carbonyl carbon of benzaldehyde.

著者

藤田 眞作

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.70, no.9, pp.951-957, 2012

被引用文献数

1

著者

川口 春馬

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.10, pp.922-931, 1984

被引用文献数

3

---

Research and development on the preparation of novel polymer microspheres and their applications have been accelerated in this decade. This article deals with polymer catalysts and reagents which have functional groups on and in polymer microspheres or beads. Immobilization of functional groups on polymer microspheres causes not only simplification of the recovery of reagent from the reaction system, but also changes in the rate, selectivity, and pattern of reaction in most cases. Dependence of these changes on the physical and chemical structure of polymer microspheres is discussed and a guide is given for the preparation of polymer microspheres having desirable functions.

著者

飛鋪 靖

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.32, no.12, pp.971-988, 1974-12-01 (Released:2009-11-13)

参考文献数

118

被引用文献数

1 3