著者

横川 文明 塩入 孝之

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.58, no.7, pp.634-641, 2000-07-01 (Released:2009-11-13)

参考文献数

29

被引用文献数

2 4

---

Antillatoxin is an ichthyotoxic cyclic lipopeptide isolated by Gerwick and co-workers from the marine cyanobacterium Lyngbya majuscula collected in Curacao. Although we have finished the stereoselective total synthesis of antillatoxin having the proposed structure with (4S, 5R) -configuration, we have found that the synthetic sample was not identical with the natural one and the proposed structure should be revised. Further our synthetic efforts have culminated in the first total synthesis of antillatoxin in its natural form, proving that the natural one has (4R, 5R) -configuration. In this account, our total synthesis and synthetic studies by other groups will be discussed.

著者

白岩 雅文 大野 雅二 長谷川 淳三

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.45, no.4, pp.396-396, 1987-04-01 (Released:2009-11-13)

著者

尾島 巌

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.58, no.5, pp.397-398, 2000-05-01 (Released:2009-11-13)

著者

山田 幸子 高山 浩明

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.46, no.9, pp.893-908, 1988-09-01 (Released:2009-11-13)

参考文献数

76

被引用文献数

7 8

---

Recent advances in the chemistry of 3- sulfolene, 2, 5- dihydrothiophene 1, 1-dioxide, are reviewed from a view point of diene synthesis. Reaction of 3- sulfolene α- carbanion generated under a variety of basic conditions with various electrophiles followed by a stereoselective desulfonylation provides a new method for synthesizing (E) -, (E, Z) -, and (E, E) -conjugated dienes with extremely high stereoselectivity. The method is applied to the syntheses of various natural products having a conjugated diene structure. 3-Sulfolenes are used as masked dienes in the syntheses of cyclic compounds including natural products via inter- and intramolecular Diels-Alder reactions. Some other developments of the chemistry of 3-sulfolenes and its benzo analogs, benzo [c] -1, 3-dihydrothiophene 2, 2-dioxides, are briefly reviewed.

著者

菊嶌 孝太郎

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.73, no.1, pp.76-77, 2015 (Released:2015-02-20)

参考文献数

13

---

In 2009, Buchwald group demonstrated the first catalytic nucleophilic fluorination to aryl fluorides in the presence of Pd-catalyst based on tBuBrettPhos with CsF as a fluoride source. Based on the significant report, the palladium-catalyzed nucleophilic fluorination system has been modified to improve the reactivity. Additionally, some groups reported the Cu-mediated and -catalyzed nucleophilic fluorination, wherein the reactions are considered to involve the formation of Cu(III) intermediates.

著者

大熊 毅 野依 良治

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.7, pp.553-563, 1996-07-01 (Released:2009-11-16)

参考文献数

32

被引用文献数

3 5

---

Enantioselective reduction of prochiral ketones to optically active secondary alcohols is an important, fundamental subject in synthetic organic chemistry, because the resulting chiral alcohols are versatile building blocks for synthesis of natural or unnatural biological active compounds as well as functional materials. Asymmetric hydrogenation is particularly useful for a large-scale reduction because of the operational simplicity, economical advantage, and environmental consciousness. Enantioselective hydrogenation of simple ketones which have no heteroatoms near carbonyl groups has remained difficult. This review describes the recent development in this area. Certain chiral Ru (II) complexes exhibit an excellent catalytic activity and enantiodifferentiation ability in asymmetric hydrogenation of simple ketones in homogeneous phase.

著者

西村 佐知夫

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.23, no.7, pp.612-619, 1965-07-01 (Released:2010-06-28)

参考文献数

73

被引用文献数

1 3

著者

内多 稔 小松 真 山崎 勝也

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.53, no.12, pp.1077-1089, 1995-12-01 (Released:2009-11-16)

参考文献数

29

被引用文献数

1 1

---

A novel series of N-acylamino acid analogues of 2 (1H) -quinolinone was synthesized and evaluated for antiulcer activity against acetic acid-induced gastric ulcer in rats. Out of this investigation, 2- (4-chlorobenzoylamino) -3- [2 (1H) -quinolinon-4-yl] propionic acid (rebamipide, OPC-12759) was identified The structureactivity relationships are discussed.Rebamipide did not only increase the healing rate of a chronic gastric ulcer model, acetic acid-induced gastric ulcer in rats, but also prevented recurrence and/or relapse of the ulcer in long term observation Rebamipide inhibited the formation of gastric mucosal lesions induced by various conditions. Rebamipide did not inhibit gastric acid secretion, although it potentiated gastric mucosal defensive factors such as mucus secretion, alkaline secretion, gastric mucosal blood flow and mucosal barrier. Rebamipide inhibited ethanol-induced gastric mucosal necrosis, which was completely abolished by pretreatment with indomethacin, suggesting the mucosal protective effect is associated with endogenous prostaglandins. Rebamipide inhibited production of superoxide from polymorphonuclear leukocytes and scavenged hydroxyl radical in vitro. Rebamipide showed useful efficacy on Helicobacter pylori-induced cell damage associated with activated neutrophils.The enantiomers of rebamipide were synthesized by using three efficient methods. Both enantiomers showed anti-ulcer activity against acetic acid-induced gastric ulcer and EtOH-induced gastric ulcer. The pair of enantiomers showed a small difference in activity.

著者

小槻 日吉三 隈本 康司

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.63, no.8, pp.770-779, 2005-08-01 (Released:2009-11-13)

参考文献数

85

被引用文献数

6 12

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The great utility of high-pressure technology to achieve the desired reactions which are not readily accessible by other means and its application in natural product or material synthesis have been reviewed. Newly developed methods especially atom-economic processes for functional group transformations, environment-friendly constructions of target molecules, and promotion of sterically-restricted organic reactions are described. These include (1) Diels-Alder reaction, (2) intramolecular Diels-Alder reaction, (3) hetero-Diels-Alder reaction, (4) 1, 3-dipolar [3+2] cycloaddition reaction, (5) aldol condensation, (6) Friedel-Crafts-type alkylation, (7) Michael addition reaction, (8) SN2-type substitution, (9) nucleophilic aromatic substitution, (10) epoxide ringopening reaction, (11) organometallic reaction, (12) Lewis acid-catalyzed reaction.

著者

喜多河 庸二

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.18, no.7, pp.453-474, 1960-07-01 (Released:2010-10-20)

著者

石井 永

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.11, pp.922-941, 1972-11-01 (Released:2010-01-22)

参考文献数

81

被引用文献数

5 6

著者

覚知 豊次 横田 和明

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.48, no.12, pp.1106-1114, 1990-12-01 (Released:2009-11-13)

参考文献数

33

被引用文献数

5 4

---

Cyclopolymerization, which does not need a cyclic derivative as monomer, is a direct method for producing rings and polymer chain at the same time. Monomers forming 5-7 membered-rings have been generally studied. We established the synthesis of polymers with macrocyclic units via cyclopolymerization of bifunctional monomers containing oxyethylene units. Poly (crown ether) s and poly (cryptande) s are synthesized through the polymerizations of divinyl ethers and diepoxides, poly (thia-crown ether) s through diepisulfides, and poly (crown lactone) s through the monomers having acrylic and allylic groups. These polymers except for poly (crown lactone) s consist essentially of cyclic constitutional repeating units, and have the cation-binding properties. Cyclopolymerization of divinyl ethers is a facile method for producing optically active poly (crown ether) s which exhibit chiral recognition towards α-amino acids. For the cyclopolymerization of divinyl ether derived from chiral 3, 3'-disubstituted- 1, 1'-bi-2-naphthol, the asymmetric induction in the polymer main chain was concluded by the analysis of 1H NMR spectra of polymers.

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.11, no.12, pp.475-478, 1953-12-30 (Released:2010-10-20)

著者

室伏 旭

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.43, no.11, pp.991-1002, 1985-11-01 (Released:2009-11-13)

参考文献数

26

被引用文献数

1

---

Plant hormones are very important bio-active compounds which regulate the physiology of higher plants. There are five kinds of known plant hormones, auxin, gibberellin, cytokinin, abscisic acid and ethylene. Besides, there are some other plant hormone-like substances as brassinolide, polyamines and unknown flower-inducing substances. The studies of plant hormones concerning activity, practical use, fluctuation of endogenous level in intact plants, biosynthesis and structure-activity relationship are explained. The organic syntheses in these studies are important especially in production of plant hormones and their related compounds enough for their application test in the agricultural field, and various kinds of derivatization of plant hormones for the investigation of action mechanism and for the modern analysis methods with highest reliability and sensitivity. Some other importance of organic synthesis in plant hormone research is discussed.

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

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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

斎藤 鐘次郎 立花 輝一 大道 弘昭

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.20, no.2, pp.150-157, 1962-02-01 (Released:2011-07-05)

参考文献数

23

被引用文献数

1

---

6-Methyl-6 (or 5)-hepten-2-one was synthesized from the addition compounds which were prepared from 4-methyl-l-penten-3-ol acetate or 2-methyl-4-penten-2-ol acetate and acetaldehyde by the Prins Reaction.These addition compounds weve at first hydrolysed to sec- or test-keto-alcohols respectively and then dehydrated to methyl heptenone under appropriate conditions in good yield. The dehydration of 6-methyl-5-hydroxy-2-heptanone was best carried out at 280-370°c by passing through a pyrex glass tube, packed with pumice catalyst containing phosphoric acid. 6-Methyl-6-hydroxy-2-hepta-none was dehydrated to 6-methyl-5-hepten-2-one with a trace of iodine. On the other hand, 6-methyl-6-hydroxy-2-heptanone acetate was subjected to pyrolysis at 450°c through a pyrex glass tube, filled with crushed glass in almost quantitative yield, giving 6-methyl-6-hepten-2-one. 6-Methyl-6-hydroxy-2-heptanone, reported by Verley in 1897, which was obtained by the hydration of methyl heptenone with 40-50% H2SO4, differed apparently from the hydrolygate of 6-methyl-6-hydroxy-2-heptanone acetate. The substance which was obtained by Verley's method, was supposed to be 2, 2-dimethyl-6-methyl-6-hydroxy-tetrahydro pyran. When 6-methyl-5-hydroxy-2-heptanone acetate was hydrolyged with alcoholic sodium hydroxide solution, 2-isopropyl-5-methyl-5-ethoxy-tetrahydrof uran and 6-methyl-5-hydroxy-2-heptanone were obtained. The f uran ring of the former could be opened easily to the latter keto-alcohol when it was boiled with dil. HCl.

著者

吉田 隆志 波多野 力 伊東 秀之

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.62, no.5, pp.500-507, 2004-05-01 (Released:2009-11-13)

参考文献数

24

被引用文献数

5 14

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Large-size secondary metabolites with dimeric-oligomeric and/or dendrine-type structure from higher plants are regarded as natural nanomolecules which are constructed in a bottom-up pathway from small molecules under biological condition. Among them are polyphenols classified as tannins which have large molecular weights ranging from 500 to 4000, and strong affinity to proteins, alkaloids and heavy metals to form complex molecules (precipitates). They constitute two major groups : one is condensed tannins (proantocyanidins), which are composed of flavan-3-ol units linked through C-C bond, and the other is hydrolyzable tannins, which are principally multiple esters of D-glucose with gallic acid and its oxidative metabolites. This paper reviews the diverse structural characteristics of both tannins, especially ellagitannin oligomers up to pentamers, and examples of their biological activities. Formation of insoluble and soluble complex between tannins and proteins are also described.

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

生長 幸之助

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.1, pp.74-78, 2014-01-01 (Released:2014-03-04)

参考文献数

14

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This article summarizes how “blog” media, which is complementary to traditional media (newspaper, television, academic journal etc.), is affecting and changing scientific communication processes especially in synthetic organic chemistry, through reviewing recent representative examples.

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

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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.