著者

島村 賢 高橋 基将 藤本 泰典 安岡 宏 伊藤 孝之

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.75, no.2, pp.121-133, 2017-02-01 (Released:2017-04-06)

参考文献数

42

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(2-Deoxy-2-fluoro-4-thio-β-d-arabinofuranosyl)thymine (S-FMAU) was synthesized very efficiently from corresponding d-arabinofuranose derivative 16a which was available in bulk. Three important transforming methods were mainly described. One was the practical inversional bromination process for secondary alcohol generated by opening furanose ring. Another was the highly efficient thiofuranose synthesis via intramolecular carbonyl assisted SN2 reaction. And the last was the β-selective glycosylation process with thymine derivative. Applications of the thiofuranose synthesis using intramolecular carbonyl assist were also discussed.

著者

新井 和孝

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.6, pp.486-498, 1986-06-01 (Released:2010-01-22)

参考文献数

52

被引用文献数

4 8

---

In recent years, synthetic method by the combination of isomerization and crystallization is studied intensively, especially in the practical optical resolution. In this paper, this isomerization-crystallization method is introduced from a point of view of practical organic synthesis. A number of examples of this isomerization-crystallization method in optical resolution, many of which were often reported as the example of second-order asymmetric transformation phenomena, are classified into following two groups, and reviewed.(1) Epimerization-crystallization method.(2) Racemization-preferential crystallization method.The potentialities and difficulities of each method are also discussed. The compounds resolved by this methods are α-amino acid derivatives, cyanohydrin derivatives, α-aromatic carboxylic acid esters, and so on.

著者

服部 達也

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.17, no.9, pp.505-512, 1959-09-01 (Released:2010-10-20)

参考文献数

52

著者

石原 一彰

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.6, pp.563-563, 2018-06-01 (Released:2018-06-06)

著者

只野 金一 石原 淳 小川 誠一郎

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.49, no.4, pp.327-339, 1991-04-01 (Released:2009-11-16)

参考文献数

62

被引用文献数

5 7

---

The [3, 3] sigmatropic rearrangement, represented by Claisen rearrangement, is one of the promising synthetic tools for the carbon framework construction in natural product synthesis. The reliability of the stereochemical issue, especially being realizable in cyclic systems, is well recognized. In this article, we summarize our recent development in the field of the Claisen rearrangements applied to the carbohydrate-derived substrates. The highly stereoselective quaternization of the ring-carbon of the furanose derivatives is also featured in this context. The utility of the rearrangement strategy was substantiated through the first total synthesis of (-) -acetomycin, an antimicrobial and antitumor agent.

著者

小野 光則

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.38, no.9, pp.836-852, 1980-09-01 (Released:2009-11-13)

参考文献数

195

被引用文献数

3 3

---

Recent progress in regioselective carbon-carbon bond forming reactions involving “ambident substrates” has been reviewed with 308 selected references. This article is divided into two parts, Part 1 concerns the reactions of ambident nucleophiles which mainly include the di-anions of enolates and the asymmetric allylic carbanions. Part 2 involves the reactions of ambident electrophiles which are represented by α, β-unsaturated carbonyl systems, the SN 2' reactions of allylic alcohol derivatives and the epoxy compounds containing a nucleophile in the same molecule. Some plausible explanations and controlling factors of these regioselectivities are summarized.

著者

大田 正樹

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.17, no.12, pp.747-755, 1959-12-01 (Released:2010-10-20)

参考文献数

71

著者

池田 大四郎 味戸 慶一

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.49, no.11, pp.1002-1012, 1991-11-01 (Released:2009-11-16)

参考文献数

46

被引用文献数

2 3

---

Anthracycline antibiotics, adriamycin, daunomycin and aclacinomycin A, have been widely used in the clinical treatment of various tumor diseases. Recently, semisynthetic anthracyclines, pirarubicin and epirubicin having improved antitumor effects and reduced adverse reactions in comparison with the parent compound, have been launched into clinical chemotherapy. Furthermore, several semisynthetic agents are under the clinical trials (phase I or phase II stage). In our search for useful and orally absorbable analogs, we synthesized a new barminomycin analog and a number of pirarubicin analogs. Barminomycins I and II have the unique eight-membered acetal-azomethine ring structure and show the strong activity in vitro. A new barminomycin analog (1) has been synthesized through the hypothetical biogenic intermediate, 4'-O-glycosyldaunomycin (22). The activity of 1 in vitro is stronger than that of the parent daunomycin. The quantitative structure-activity relationships of orally absorbable pirarubicin analogs are also discussed. The gastrointestinal absorption of salicylidene analogs of pirarubicin depends on the van der Waals volume of the substituent (s) on the salicylidene moiety and the polarity of the molecule.

著者

上野 義仁 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.61, no.9, pp.890-899, 2003-09-01 (Released:2009-11-13)

参考文献数

59

被引用文献数

2 4

---

最後に, 筆者らが合成したアナログを含むオリゴヌクレオチドの性質を図11 (+は二本鎖の熱的安定性あるいはヌクレアーゼ耐性が未修飾のオリゴヌクレオチドと比較して高いことを, 一は低いことを示す) にまとめて示した。糖部4ノα位にアミノエチル側鎖を導入したヌクレオシドを含むオリゴヌクレオチドは, 相補鎖RNAとの二本鎖の熱的安定性を若干低下させるものの, エンドおよびエキソの両ヌクレアーゼに対して高い耐性を示すこと, またRNase H活性を誘導することから現在リン酸ジエステル結合型アンチセンス分子として最も有望であると考えている。

著者

梅澤 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.49, no.11, pp.1062-1069, 1991-11-01 (Released:2009-11-16)

参考文献数

31

被引用文献数

1 2

---

Streptomyces and other microorganisms produce antibiotics, anticancer agents and enzyme inhibitors as secondary metabolites. Microorganisms are a treasury of organic compounds which have various structures and biological activities. Therefore, isolation of the specific bioactive products in culture broths is dependent upon the testing method. Since oncogene theory has been extensively developed, we have screened oncogene function inhibitors as a new group of microbial secondary metabolites. Oncogene functions include acting as a modified growth factor receptor (erb B, erb B 2 fms), acting as a growth factor itself (sis, hst), the tyrosine kinase activity (src oncogene group), and acting as a G protein to activate phosphatidylinositol turnover (ras).Erbstatin is an inhibitor of erb B, erb B 2 and src products-associated tyrosine kinase. In cell culture it inhibited EGF receptor internalization, delayed the onset of EGF-induced DNA synthesis in quiescent cells, and induced normal phenotypes in src oncogene expressing cells. It inhibited the growth of human breast and esophageal carcinomas in nude mice. Lavendustin A was isolated from Streptomyces as a potent inhibitor of tyrosine kinase. It is a novel compound and about 50 times stronger than erbstatin in in vitro inhibition of tyrosine kinase. Many oncogenes including ras, src, sis, fms, and fes are considered to activate cellular phosphatidylinositol turnover. We have isolated psi-tectorigenin, inostamycin and piericidin B1 N-oxide as inhibitors of inositol incorporation into phospholipids. Thus, various inhibitors of oncogene functions including novel structures have been discovered in microbial secondary metabolites. They are useful for the dynamic study of oncogenes.

著者

金子 正勝 清水 文治

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.37, no.1, pp.40-56, 1979-01-01 (Released:2009-11-13)

参考文献数

120

被引用文献数

1 3

---

Synthetic procedures of arabinofuranosyl nucleosides, especially, of arabinofuranosyl purine nucleosides are reviewed from the following points of view; i) methods which include nucleoside epoxide as an intermediate ii) direct condensation methods of arabinose derivatives and various purine bases iii) methods which include purine-8-cyclonucleosides as an intermediate and iv) other methods. Biological activities of arabinofuranosyl purine nucleosides are also summarized briefly.

著者

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.48, no.10, pp.907-920, 1990 (Released:2009-11-13)

参考文献数

135

被引用文献数

11 12

---

Recent development in synthetic chemistry of the sugar moiety of nucleosides as potential anti-HIV agents has been reviwed. These include the chemical transformation of the sugar moiety of naturally-occurring nucleosides and the synthesis of carbocyclic nucleosides. Total syntheses of (-) -oxetanocin and its derivatives are also discussed.

著者

池原 森男 福井 寿一

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.37, no.11, pp.948-959, 1979-11-01 (Released:2009-11-13)

参考文献数

82

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Application of nucleic acid chemistry to drugs is discussed. The article contained 1) a survey of nucleobase and nucleoside analogs, which are used to anticancer and antiviral diseases ; 2) Application of oligo- and polynucleotides to medical purpose ; and 3) Use of gene recombinant technique for producing hormones etc.

著者

藤本 正治

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.57, no.5, pp.374-381, 1999-05-01 (Released:2009-11-16)

参考文献数

9

被引用文献数

2 3

---

Cefotetan (YM09330) is a semi-synthetic injectable antibiotic which was discovered and developed by Yamanouchi Pharmaceutical Co., Ltd. and has been on the market since 1983. This compound shows a strong and wide spectrum of antibacterial activity and high stability against β-lactamase This paper outlines the optimization of the synthetic process, the replacement of the trifluoroacetic acid used for the cleavage method of benzhydryl ester, work on the stability of diphenyldiazomethane, an alternative synthetic route to Cefotetan, the method for synthesizing the isothiazole derivative and the scale-up of Cefotetan synthesis.

著者

中崎 昌雄 苗村 浩一郎

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.40, no.12, pp.1128-1144, 1982

被引用文献数

6

---

We have been interested in the chemistry of the gyrochiral cage-shaped molecules possessing <I>D</I><SUB>3</SUB>- twisted bicyclo [2.2.2] octane molecular framework as a common structural unit, and this article summarizes our recent studies on the synthesis, stereochemistry, and biological transformation of this unique group of cage-shaped molecules on which a generic name "triblattane", has been coined to characterize their common structural feature.

著者

中崎 昌雄 山本 浩司

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.39, no.7, pp.624-632, 1981-07-01 (Released:2009-11-13)

参考文献数

43

被引用文献数

1 3

---

1977 witnessed almost simultaneous announcements of two completely independent syntheses of trans-doubly bridged ethylenes, one from Osaka University group and the other from Northwestern University group.This review provides a critical survey on the recent development in the chemistry of this unique and fascinating class of cyclic compounds with unsaturated center buried in the molecular cavity.

著者

岩渕 好治 畑山 範

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.60, no.1, pp.2-14, 2002-01-01 (Released:2009-11-13)

参考文献数

47

被引用文献数

39 57

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The Morita-Baylis-Hillman reaction, α-hydroxyalkylation of activated olefins, has attracted considerable research interest because of the synthetic utility of the densely functionalized product as well as the exquisite tandem Michael-aldol reaction process under nucleophilic catalysis. This review gives an overview on recent remarkable progress in the Morita-Baylis-Hillman reactions. Several other successful methods affording the Morita-Baylis-Hillman type adducts are also reviewed by focusing their imaginative strategies.

著者

若林 秀夫

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.48, no.2, pp.164-166, 1990-02-01 (Released:2009-11-13)

被引用文献数

1 2

---

乳酸は, 旧約聖書の創世紀の頃からすでに知られており, 化学的に単離したのはSheele (1780) で, 発酵した牛乳からシロップ状の酸を得て, 乳酸と命名した。またBerzelius (1807) は, 筋肉中よりこれによく似た酸 (d-酸) を分離したが, この二つの酸が同一物質であることはWislicenusにより1873年にようやく証明された。即ちSheeleの乳酸はラセミ体で光学活性のない乳酸であり, 筋肉から得られたものは右旋光性の乳酸(d-乳酸) であった。このように乳酸にはL体とD体の光学異性体と, 光学活性のないDL体が存在する。また乳酸と言えば通常α-オキシ・プロピオン酸CH3CH (OH) COOH (分子量C3H6O3=90.08) のことを言う

著者

桐生 知男

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.17, no.9, pp.564-568, 1959-09-01 (Released:2010-10-20)

参考文献数

23

著者

浅原 時泰

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.6, pp.728-729, 2014-06-01 (Released:2014-07-16)

参考文献数

12

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Nitroso compounds have drawn much attention of synthetic organic and biological chemists because of their usefulness as synthetic intermediate as well as interesting bioactivity. Here, a recent report about the simple and selective preparative method for nitrosoarenes using nitrosonium tetrafluoroborate is described. It provides versatile nitrosoarenes including heteroarenes which are not easily prepared by alternative method.