著者

梅野 正行 浜田 三夫

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.38, no.12, pp.1196-1209, 1980-12-01 (Released:2010-01-22)

参考文献数

118

被引用文献数

1

---

This article reviews some of recent applications of the Grignard reaction to synthesis of alcohols, ketones, aldehydes, acetals, carboxylic acides, esters, ethers, amino, compounds, organo sulfer compounds, vinyl compounds, acetylenic compounds, and organometalic compounds.A number of compounds produced by the Grignard reaction are very valuable and special intermediates or products in the field of pharmaceutical, perfume, and other fine or specialty chemicals.Synthesis of many optically active compounds by the reaction of sec-alkyl Grignard reagents with alkenyl halides using chiral phosphine-metal complexes as catalysts has been receiving great attention.

著者

熊谷 直哉

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.77, no.6, pp.616-626, 2019-06-01 (Released:2019-06-11)

著者

田中 耕作三世 小林 健一 古源 寛

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.77, no.7, pp.673-683, 2019-07-01 (Released:2019-07-08)

参考文献数

34

被引用文献数

3

---

(−)-L-755,807, which was isolated from an endophytic fungus, Microsphaeropsis sp., consists of a characteristic epoxy-γ-lactam ring and a tetraene-containing side chain, and exhibits bradykinin B2 receptor antagonist activity. The first total synthesis of (−)-L-755,807 was accomplished through a convergent approach, employing a late-stage coupling between the ring and side-chain segments. The ring segment was efficiently synthesized by a novel syn-selective Darzens reaction between di-tert-butyl bromomalonate and α-alkoxy aldehyde, and the side-chain segment was prepared by a highly stereoselective Horner-Wadsworth-Emmons reaction as a key step to construct the tetraene part. This synthesis enabled us to assign the relative and absolute configurations of (−)-L-755,807. Furthermore, we discovered an additional biological activity of this compound, namely, potent amyloid β aggregation inhibitory activity, which could be useful in the treatment of Alzheimer’s disease. The epoxy-γ-lactam moiety was identified as a likely pharmacophore for this activity. In this article, we describe the total synthesis, stereochemical assignment, and biological evaluation of (−)-L-755,807.

著者

北口 博司

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.53, no.5, pp.381-391, 1995-05-01 (Released:2009-11-16)

参考文献数

59

被引用文献数

1

---

In the past decade, in has been established that enzymes exhibit high catalytic activity as a solid state in organic solvents containing little or no water. Because organic solvents are better reaction media than water for most synthetic transformations, such has been applied to a number of organic reactions.This article is intended to provide mechanistic understanding of this phenomenon, which counters conventional wisdom. The key concept here is the high rigidity of protein's conformation under limited water content conditions : the balance of its thermodynamic stability and kinetic rigidity is essential for the enzyme's high catalytic activity and selectivities in organic media. Some applications for organic synthesis are also presented.

著者

菊池 修

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.8, pp.678-688, 1979-08-01 (Released:2010-01-22)

参考文献数

42

被引用文献数

7 6

---

The reaction mechanisms of the O-O cleavage of organic peroxides, hydrogen peroxide, hydroperoxides, dialkyl peroxides, peracids, peroxyesters, and diacyl peroxides, have been explained on the basis of their HOMO and LUMO and on the basis of the potential surfaces along the reaction paths.The discussion covers the electronic structure and conformation of the peroxides, the characteristics of HOMO and LUMO of the peroxides, the reaction with nucleophiles and with electrophiles, homolytic decomposition process, radical-induced decomposition, and the electronic structure of the radicals produced from the O-O cleavage.

著者

増野 匡彦

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.58, no.12, pp.1202-1209, 2000-12-01 (Released:2009-11-13)

参考文献数

23

被引用文献数

1 1

---

We have found a novel metabolic pathway of phenols catalyzed by cytochrome P450 and its chemical models. When various p-substituted phenols (substituent = OPh, NO2, CN, CH2OH, COCH3, COPh, COOH, F, Cl, and Br) were reacted with rat liver microsomes system or meso-tetraphenylporphinatoiron (III) chloride model system, the substituent was eliminated to produce hydroquinone. In the case of p-cresol, p-toluquinol was formed instead of hydroquinone. To elucidate how the substituent is eliminated, we attempted to detect the product derived from the eliminated group. Results indicated that the mechanism of this reaction can be divided into two types : the substituent is eliminated as an anion and as a cation. P450 also catalyzed phenol coupling reaction to give biphenyl derivatives, diphenyl ether derivatives, and dibenzodioxin.

著者

森田 桂

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.5, pp.375-381, 1977-05-01 (Released:2009-11-13)

参考文献数

67

被引用文献数

3 3

---

The unpleasant odor of sulfur-containing organic substances has long been an annoyance to human beings as exemplified by the fact that the stench issued by the skunk is represented by 1-butanethiol and that many other mercaptans and hydrogen sulfide are currently under severe environmental regulations.By the advent of recent chromatographic separation techniques together with micro-analytical tools, a variety of pleasant and unpleasant odorous substances have been isolated and characterized as being the aroma-bearing substances of many kinds of foods.The present paper reviews these sulfur-containing substances in relation with their characteristic aroma of beef, “shiitake” an edible mushroom (Lentinus edodes Sing.), “sho-yu” a Japanese Soy-Sauce, tomato, potato and potato chips, coffee, cocoa, roasted nuts, bell peppers, and others.

著者

中村 公一

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.45, no.2, pp.171-172, 1987-02-01 (Released:2009-11-13)

著者

太田 博道

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.41, no.11, pp.1018-1030, 1983-11-01 (Released:2010-01-22)

参考文献数

119

被引用文献数

3 4

---

Recently, organic syntheses are directed toward very complex compounds and hence the development of highly selective reactions is required. Thus, it becomes increasingly important to utilize enzymatic reactions as key steps in organic synthesis. This article reviews the recent topics in microbial and enzymatic oxidations of organic compounds and their application to the synthesis of physiologically active compounds. The application of the biological systems are classified into types of reactions including, a) oxidation of saturated C-H bonds, b) oxidation of unsaturated bonds, c) oxidation of alcohols, d) oxidation of sulfides. Emphasis is placed to the chemo-, regio-, and stereo-selectivities of the reactions. Reductive reactions containing C-C bond formations are also described briefly.

著者

太田 博道

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.8, pp.726-741, 1988-08-01 (Released:2010-01-22)

参考文献数

199

被引用文献数

15 13

---

Microbial and enzymatic transformation of synthetic substrates is attracting much attention as a useful method in synthetic organic chemistry. In this article, recent developements in this field are reviewed, dividing into three major sections which include oxidation, reduction and hydrolysis reactions. Methods for increasing the selectivity of some reactions are also described. Emphasis has been placed to the formation of optically active compounds, because enzymes are able to catalyze asymmetric reactions under mild conditions.

著者

寺島 孜郎

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.31, no.5, pp.353-374, 1973-05-01 (Released:2009-11-13)

参考文献数

106

被引用文献数

4 4

著者

鶴巻 英治

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.4, pp.360-361, 2017-04-01 (Released:2017-04-28)

参考文献数

10

---

Carborane acid is the strongest Brönsted acid presently known, possessing unusually high acidity greater than fluorosulfuric acid. Protonation by a carborane acid have proceeded effectively towards the weakest bases such as benzene, fullerene, alkanes, and even carbon dioxide, producing corresponding reactive cations as salts with the least coordinating carborane anion. This short-review highlights recent reports on structural elucidations of several important cations using a carborane acid.

著者

池原 森男 上田 亨

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.6, pp.402-418, 1974-06-01 (Released:2010-01-21)

参考文献数

123

被引用文献数

5 7

著者

四方田 隆

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.10, pp.918-919, 1995-10-01

著者

森 謙治

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.509-510, 2000-05-01 (Released:2009-11-13)

参考文献数

4

著者

飛田 満彦

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.22, no.5, pp.339-356, 1964-05-01 (Released:2010-06-28)

参考文献数

105

著者

村田 道雄 安元 健

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.3, pp.207-217, 1995-03-01 (Released:2010-01-28)

参考文献数

27

被引用文献数

1 3

---

Maitotoxin was first discovered as one of the causative toxins responsible for ciguatera, which is a form of seafood poisoning prevalent in coral reef area. The structure (1) has been elucidated to be a polyketide compound with a molecular weight of 3422 Da, which makes the toxin the largest natural non-biopolymer known to date. The structure is partly reminiscent of brevetoxins or ciguatoxins, which comprise trans-fused polycyclic ethers, though maitotoxin possesses about three times as many ether rings as does brevetoxin B. In this paper we review the structure elucidation of maitotoxin with the main focus on spectroscopic methodology, particularly on tandem mass spectrometry (MS/ MS), three-dimensional NMR spectra, and stereostructural analysis using NOE and 3J/H.H data coupled with force field calculations.Collisionally Activated Dissociation (CAD) MS/MS spectra with a negative FAB ionization were successfully measured for fragment B (MW. 2328 Da) of maitotoxin and revealed fragment ions from which the sizes and sequences of ether rings easily were derived. Three dimensional NOESY-HMQC with pulse field gradient was determined for a 13C-enriched specimen (at about 4%) and provided 64 13C-edited NOESY spectra, some of which brought essential NOE information regarding the mode of ether cyclization and stereochemistry.

著者

伊藤 敏幸 高木 由美子

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.52, no.1, pp.59-71, 1994-01-01 (Released:2009-11-16)

参考文献数

40

被引用文献数

2 3

---

This review describes efficient means of preparing optically pure compounds via bakers' yeast mediated reaction or lipase-catalyzed reaction : (1) Bakers' yeast mediated reaction of cyanoketone was demonstrated and was discovered a new type of C-C bond forming reaction. (2) Hydrolysis of 2-substituted-3-acetoxy esters by Aspergillus lipase (lipase A 6) was demonstrated. According to summarize the stereo favoritism between substrates, the active site model of an Aspergillus lipase is proposed. (3) A simple preparation of optically active α- or γ-hydroxystannanes using Pseudomonas lipase (lipase PS) was realized. (4) Two effective means were discovered for enantioselective reaction of lipase PS : one is the modification of the acyl group by a sulfur functional group and the other is addition of a catalytic amount of l-methioninol or crown ether derivatives to the reaction mixture. (5) Optically pure (R) -4-hydroxy-3- (3, 4-methylenedioxyphenyl) methylbutanenitrile, obtained by this reaction, was applied to the synthesis of three anti-tumor lignans. (6) As a new chiral building block for tertiary alcohols, (R) -2-ally1-2- (phenylthio) methyloxirane was synthesized via lipase-catalyzed reaction.

著者

池田 正澄 田村 恭光

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.1, pp.10-21, 1980-01-01 (Released:2009-11-13)

参考文献数

78

被引用文献数

6 10

---

The synthetic utility of the Polonovski reaction has recently been widely explored. Besides classical use in dealkylation of tertiary amines and in the preparation of enamines, it can also be used in the syntheses of a Mannich reagent and many indole alkaloids. Success in the syntheses of vinblastine and related compounds is one of the most important developments. The present review summarizes the synthetic applications of this reaction.

著者

村上 幸人 青山 安宏

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.34, no.11, pp.818-827, 1976-11-01 (Released:2009-11-13)

参考文献数

6

---

The essential trace metals incorporated into metalloenzyme systems are Cr, Mn, Fe, Co, Cu, Zn, and Mo. Among other metal ions which are known to exist in biological systems in larger concentrations, Ca and Mg are also involved in enzymatic functions. The bonding forms in connecting substrate, enzyme, and metal were classified into three major categories. The stabilities of coordinate bonds were discussed in terms of the interactions between Lewis acids and bases of soft and hard nature. The typical coordination geometries of essential metals involved in biological functions were also given. The catalytic functions of nuclear metals were tentatively attributed to electronic, stereo-chemical, and oxidation-reduction effects and explained by referring to several well-qualified examples. The emphasis has been made on the hydrophobic field effect provided by apoenzymes for the development of catalytic functions of nuclear metal ions as well as on the cooperative catalytic effects by specific functional groups of apoenzymes placed in the active centers.