著者

柴崎 正勝 池上 四郎

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.7, pp.602-617, 1982-07-01 (Released:2009-11-13)

参考文献数

101

被引用文献数

1 1

---

This article describes recent total synthesis of natural products, in which highly stereo-and regioselective reactions by internal chelation with metal salts are involved. The first part of the report presents a number of total syntheses of natural products, which use highly stereoselective carbon-carbon bond forming reactions by internal chelation with metal salts. In the second part, natural product synthesis, which involves highly stereoselective reductions by internal chelation, is discussed. The final two parts of the article present synthesis of natural products, in which chelation-controlled regioselective reactions are included.

著者

久野 耕一

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.40, no.6, pp.592, 1982-06-01 (Released:2009-11-13)

著者

猪居 武 永井 洋一郎

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.6, pp.582-590, 1982-06-01 (Released:2009-11-13)

参考文献数

61

被引用文献数

2 2

---

Through many years, silicon has been considered to be biologically inactive.However, the developement in the field of organosilicon compounds has revealed that silicon is an essential element in the metabolic system.The present brief review is concentrated on the following items : a) A short survey of silicon compounds concerning life and its environment.b) A survey on a specified field of bioactive silicon compounds which have unique structures.c) A survey on a selected area of bioactive organosilicon compounds having analogous structures to bioactive parent carbon compounds.

著者

荒井 正俊

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.6, pp.567-574, 1982-06-01 (Released:2009-11-13)

参考文献数

25

被引用文献数

1 1

---

Organosilicon chemicals have been widely applied to the various industries.In this paper, the articles dealing with preparation of silanes and siloxanes in view of silicone industry, and application of silylating agents and silane coupling agents are reviewed (23 ref.).

著者

細見 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.40, no.6, pp.545-553, 1982-06-01 (Released:2009-11-13)

参考文献数

62

被引用文献数

5 7

---

Iodotrimethylsilane which has a hard acid (Me3Si) -soft base (I) bond displays a strong oxygenophilicity towards ethers, esters, lactones, acetals, and other molecules involving oxygen atom as a functional group. Recent progress of the chemistry of iodotrimethylsilane is reviewed especially from a view point of organic synthesis. The application of bromotrimethylsilane to organic synthesis is also discussed briefly.

著者

鈴木 正昭 野依 良治

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.40, no.6, pp.534-544, 1982-06-01 (Released:2009-11-13)

参考文献数

77

被引用文献数

5 5

---

Trialkylsilyl triflates are a new class of super-reagents, which act as efficient agents for silylation of active hydrogen compounds and catalysts of nucleophilic addition and displacement reactions in aprotic media. The synthetic utility is exemplified by a variety of functional group transformations and carbon-carbon bond-forming reactions. Immobilization of the silyl reagent on a resinsulfonic acid is also described.

著者

落合 正仁 藤田 栄一

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.40, no.6, pp.508-517, 1982-06-01 (Released:2009-11-13)

参考文献数

42

被引用文献数

3 4

---

The reactions of allylsilanes are discussed in terms of the allyl anion equivalents, the allyl cation equivalents, and olefins. The reactions concerning with the latter two were developed recently by the authors. The major discussion is focused on these new type reactions.

著者

熊田 誠

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.6, pp.462-471, 1982-06-01 (Released:2009-11-13)

参考文献数

177

被引用文献数

4 4

---

After a brief historical survey of organosilicon chemistry, the latest developments in this area are reviewed. Selected topics are : stereochemistry and mechanisms of nucleophilic substitutions at silicon; asymmetric syntheses of organosilicon compounds; organofluorosilanes and -fluorosilicates; utilization of the “disilane fraction” produced by the direct synthesis of methylchlorosilanes; organopolysilanes; silyl metal compounds; silicon-containing small ring systems; divalent silicon species; double-bonded silicon species; and silicon in organic synthesis.

著者

相原 良平

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.5, pp.447, 1982-05-01 (Released:2009-11-13)

著者

妹尾 鹿造

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.35, no.6, pp.497-504, 1977-06-01 (Released:2010-01-22)

参考文献数

21

被引用文献数

1 1

---

Nylon was industrially produced by du Pont for first time shortly before World War II. Hexamethy lenediamine (HMD) is a nylon-66 intermediate.Many reports on manufacturing process for HMD have been published and almost all of them now in industrial process go through the three routes, namely via adiponitrile (ADN) by using AN. butadiene or ADA as the starting material. Now among them, the method employing ADA is used most widely, but AN electrolytic hydrodimerization process and new hydrocyanation process for reacting butadiene and hydrogencyanide are developed to eliminate the defects of conventional methods, New hydrocyanation process was recently developed by du Pont and is now believed comercialised.

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.40, no.4, pp.307-320, 1982-04-01 (Released:2009-11-13)

参考文献数

69

被引用文献数

5 6

---

Preparative methods (P), reactions (R), and synthetic applications (S) of quinone bisacetals (I) and monoacetals (II) are reviewed. P-I : (1) electrochemical methods (anodic oxidations) and (2) organochemical methods ; : (1) hydrolysis, (2) hydrogenations, (3) reactions with nucleophiles, and (4) reactions of lithio derivatives of I ; and S-I : (1) isoprenoid quinones and (2) anthracyclinones. P-II : (1) electrochemical methods, (2) organochemical oxidation of p-alkoxyphenols, (3) partial hydrolysis of quinone bisacetals, and (3) hydrolysis of the monoacetals of p-quinone monosulfonimides or nucleophilic reactions of o-quinone monosulfonimides ; R-II : (1) nucleophilic additions, (2) 1, 4-additions of carbanions, and (3) reductions ; and S-II : (1) bishomoquinone and triasteranetrione, (2) tropolones, (3) neolignans, (4) cherylline, (5) anthracyclinones, (6) gymnomitrol, (7) asatone, (8) ryanodol, and (9) α-tocopherol.

著者

吉村 寿次 佐藤 憲一

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.40, no.5, pp.415-426, 1982-05-01 (Released:2009-11-13)

参考文献数

72

被引用文献数

2 2

---

Stereoselectivities in the nucleophilic addition of various nucleophiles to various 2-, 3-, 4-uloses were examined, and discussions were made on the possible, conformational change of substrates and on the following, three, main factors to control the stereoselectivities depending on the nature of reactions ; a) non-bonded interactions, after the preceding, conformational change by the coordination of magnesium to the C=O and adjacent C-O oxygens (methylmagnesium iodide) or by the solvent-dependent, dipole repulsion between the C=O and C-O bonds (methyllithium), b) intramolecular, electrostatic, attractive force between an axial oxygen or lone-paired electron of ringoxygen and diazomethyl cation in the transition states (diazomethane), c) thermodynamical stabilities of epimers to be produced in equilibration reaction.

著者

野本 享資 大船 泰史

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.5, pp.401-414, 1982-05-01 (Released:2009-11-13)

参考文献数

42

被引用文献数

18 23

---

Mugineic acid (1), an amino acid isolated from the roots of water-cultured barley (Hordeum vulgare L. var. Minorimugi), is the first phytosiderophore to be shown to play a role in the uptake and transport of iron in higher plants. The structure of 1 was determined as 2 (S), 2' (S), 3' (S), -3'' (S) -N- [3-carboxy-3- (3-carboxy-3-hydroxypropylamino) -2-hydroxypropy1] -2-azetidine-2-carboxylic acid by a direct X-ray crystallographic method, and chemical and physico-chemical studies of the degradated products of 1. Structures of other analogous amino acids from some graminaceous plants were also elucidated.Stereospecific total syntheses of 2'-deoxymugineic acid (9) and avenic acid A (11) were achieved by using common key intermediate 28 obtained from L-α-hydroxy-γ-butyrolactone (17) in short steps. N-Alkylation procedure by means of sodium cyanoborohydride in neutral media were effective for condensation of optically active units (e. g. 16c+24 25).The N, O-protecting groups were removed in two steps at the final stage of the synthesis.The structures and properties of metal complexes of mugineic acid were examined by X-ray crystallographic analysis, the potentiometric titration, spectroscopic, and electrochemical studies.

著者

染井 正徳

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.5, pp.387-400, 1982-05-01 (Released:2009-11-13)

参考文献数

70

被引用文献数

11 15

---

Various new methods for the synthesis of 4-substituted indoles were developed. These involved a) three step synthesis of N-methyl-1, 3, 4, 5-tetrahydropyrrolo [4, 3, 2-de] isoquinolines, b) one step synthesis of 4-methylaminomethylindole, c) one pot sythesis of 4-hydroxymethylindole, d) the synthesis via 4-indolediazonium salts.Short step synthesis of ergot alkaloids, (±) -6, 7-secoagroclavine, was also achieved by 5 routes, utilizing such novel reactions as a) selective mono-alkylation of nitroalkanes with gramines, b) γ-alkylation of allyl alcohol with nitroalkanes, and c) reductive alkylation of nitroalkanes with Grignard reagents.

著者

山本 嘉則 丸山 和博

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.4, pp.332-342, 1982-04-01 (Released:2009-11-13)

参考文献数

56

被引用文献数

5 5

---

The currently available methods via allylic organometallic compounds for the stereoselective synthesis of homoallyl alcohols are summarized. Usually, Z-allylic organometallics give erythro adducts upon treatment with aldehydes, while E-derivatives afford threo products. Interestingly, allylic stannanes react with aldehydes in the presence of BF3·OEt2 to give erythro products regardless of the geometry of the double bond. A short and stereoselective synthesis of the Prelog-Djerassi lactone is realized via this method. The metal effect on the stereoselection of enolate reaction is also summarized. Zirconium and tin enolates give erythro aldols irrespective of the enolate geometry. α-Mercurioketones undergo a. rapid reaction with aldehydes in the presence of BF3·OEt2 to give the kinetic erythro aldols. These erythro selections are explained by the acyclic mechanism.

著者

森 裕二

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.4, pp.321-331, 1982-04-01 (Released:2009-11-13)

参考文献数

44

被引用文献数

11 13

---

This article describes the asymmetric inductions in the intermolecular asymmetric Diels-Alder reactions. The reactions are classified into three groups : 1. Reactions of chiral dienophiles with dienes.2. Reactions of chiral dienes with dienophiles.3. Reactions catalyzed by chiral catalysts.The relationships between the absolute configuration of the chiral reagents and that of the products is discussed.

著者

長 秀連

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.4, pp.296-306, 1982-04-01 (Released:2009-11-13)

参考文献数

40

被引用文献数

3

---

Maytansine, an extraordinary antitumor agent, was stereoselectively synthesized in 1980 by Corey group. The remarkable strategy, the new reagents and reactions of the total synthesis are explained in detail here. Also, the syntheses of maytansinoids by Meyers group are briefly mentioned.

著者

尾崎 庄一郎

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.4, pp.285-295, 1982-04-01 (Released:2010-01-22)

参考文献数

112

被引用文献数

6 9

---

New isocyanates, new synthetic methods of isocyanates, new reactions of isocyanates and industrial applications of isocyanates are reviewed, based on primary journals and Chemical Titles published in recent 10 years.

著者

山田 恵敏 竹下 徹斎 田中 順太郎

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.4, pp.268-284, 1982-04-01 (Released:2009-11-13)

参考文献数

137

被引用文献数

17 22

---

Phenols, quinones, chromans, and chromens which have polyprenyl units as the side chains in aromatic compounds, are widely distributed in the natural products and many of these compounds are known as biologically active compounds. This review deals with recent advances in the syntheses of Vitamin E (α-tocopherol and α-tocotrienol), Ubiquinones (Coenzyme Q) and Vitamin K (K1 and K2).

著者

山崎 康男 増田 昭夫

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.40, no.3, pp.218-226, 1982-03-01 (Released:2009-11-13)

参考文献数

36

被引用文献数

2 5

---

Carbonylations of benzyl alcohol and its related compounds are introduced from synthetical and mechanistic viewpoints in conformity with the authors' investigation. Benzyl alcohol is easily carbonylated to form phenylacetic acid in the presence of rhodium chloride and methyl iodide, and the introduction of an electrodonating group into phenyl ring of the alcohol accelerates the reaction. A mechanistic discussion of the reaction is evolved with reference to the oxidative addition of benzylic halides to palladium complexes. In the reaction of benzyl acetate catalyzed by rhodium chloride and methyl iodide phenylacetic acid is unexpectedly formed as the main product, and a mechanistic proposal for the phenonenon is drawn.