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

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

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.

著者

池田 正之

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.33, no.5, pp.347-369, 1975-05-01 (Released:2009-11-13)

参考文献数

97

著者

小野 昇 加治 有恒

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.2, pp.115-127, 1980-02-01 (Released:2009-11-13)

参考文献数

110

被引用文献数

21 24

---

Recent advances of the chemistry of aliphatic nitro compounds are reviewed, in which the following items are covered. 1) Preparation of aliphatic nitro compounds. 2) Reaction of aliphatic nitro compounds which includes substitution and elimination reaction of the nitro group, conversion of the nitro group to the carbonyl or amino group and organic synthesis using nitroolefins.

著者

北 泰行 田村 修 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.44, no.12, pp.1118-1133, 1986-12-01 (Released:2009-11-13)

参考文献数

201

被引用文献数

12 16

---

Silyl ketene acetals (SKA) have attracted much attention as useful synthetic reagents. This review deals with the recent studies (mainly after 1980) on the preparations and reactions utilizing SKA in the following items with 147 references; [1] Preparations; a) general preparation, b) selective synthesis of E- and Z- SKA. [2] Reactions; a) protonation, b) oxidation, c) electrophilic substitution, d) cycldaddition, e) sigmatropic reaction, f) others.

著者

鈴木 啓介 長澤 徹哉

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.5, pp.378-390, 1992-05-01 (Released:2010-01-28)

参考文献数

114

被引用文献数

34 32

---

The present article deals with a short review on the recent methodological progress in O-glycoside synthesis. Particular stress is laid on the design of newer classes of glycosyl donor, which allow the selective activation/O-glycoside formation under specific reaction conditions. Based on the anomeric leaving group, glycosyl donors are classified into nine classes, 1) fluoride, 2) thioglycoside, 3) O-acylate, 4) O- and S-carbonate derivatives, 5) phosphate derivatives, 6) trichloroacetimidate, 7) 1-hydroxyl sugar, 8) 4-pentenyl glycoside, 9) glycal, and their selective activation methods are tabulated. Also described are the other approaches based on different principles, e.g., glycosylidene carbene, anomeric O-alkylation, internal cyclization or glycoside synthesis based on physical means;light, electric, thermal, and high pressure. Recent topics in this field are also included, 1) new protecting groups, 2) stereochemical control in manno- and 2-deoxy-sugars, and 3) the armed/disarmed concept.

著者

田村 恭光 北 泰行

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.3, pp.205-217, 1988-03-01 (Released:2009-11-13)

参考文献数

57

被引用文献数

11 13

---

Anthracycline antibiotics are important antitumor agents in clinical use and much attention has been paid to the synthesis of these antibiotics and related compounds. In this article, authors explain new and facile cycloadditions of homophthalic anhydrides and application of these reactions to highly regiospecific syntheses of naturally occurring anthracycline antibiotics and related anthracyclines. This review contains the following items with 57 references; [1] Cycloaddition of homophthalic anhydrides; a) thermal cycloaddition, b) strong base-induced cycloaddition. [2] Synthesis of anthracyclines; a) 4-demethoxydaunomycin and daunomycin, b) 11-deoxydaunomycin, c) adriamycin-type anthracycline, d) optically active anthracyclinone, e) amino sugars. [3] Synthesis of D-ring heteroaromatic analogues of anthracyclines.

著者

田中 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.63, no.4, pp.351-358, 2005-04-01 (Released:2009-11-13)

参考文献数

31

被引用文献数

14 17

---

A novel intramolecular trans-hydroacylation of 4-alkynals leading to cyclopentenones was accomplished by using a cationic rhodium (I) complex. We also developed three types of new reactions, 1) reaction of 4-alkynals with phenol to provide cis-4-alkenoates, 2) [4 + 2] cycloaddition of 4-alkynals with alkynes to provide cyclohexenones, and 3) isomerization of 4-alkynals to 1, 3-dienals, through five-membered rhodium metallacycles generated from 4-alkynals. The asymmetric variants of this intramolecular hydroacylation reaction were successfully developed by using 3-methoxy-4-alkynals as the substrates. The present method represents an attractive new route to highly functionalized cyclopentenones and cyclobutanones.

著者

酒井 浄

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.51, no.8, pp.733-743, 1993-08-01 (Released:2009-11-16)

参考文献数

41

被引用文献数

11 13

---

Rh (I) -catalyzed cyclization of substituted 4-pentenals into cyclopentanones found first by our laboratory was developed into the highly diastereoselective and enantioselective asymmetric cyclization by using the Rh (I) -complex with chiral ligand such as BINAP, and (+) -DIPMC. Cationic Rh (I) with BINAP afforded the best asymmetric cyclization in chemical yields and enantioselectivity as well as the diastereoselectivity. This cyclization method could be successfully applied for the synthesis of iridomyrmecin and isoiridomyrmecin from (-) -i-monene. In addition, Rh (I) -catalyzed cyclization of oct-6-enal with the cis-cyclohexane-1, 2-dioxy function at C 3-position afforded two conformational diastereomers due to a cis-cyclohexane-1, 2-diol moiety. The interesting findings found by our group are summarized as main topics in this paper.