著者

赤井 周司 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.65, no.8, pp.772-782, 2007-08-01 (Released:2010-10-20)

参考文献数

52

被引用文献数

12 13

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The lipase-catalyzed transesterification of alcohols with acyl donors in organic media has gained increased attention as a powerful method for the preparation of optically enriched compounds under very mild conditions, in which the vinyl esters 2 have been most frequently employed as the acyl donors; however, they are not always satisfactory.We applied the ethoxyvinyl esters 6 to the lipase-catalyzed transesterification reactions for the first time and discovered their advantages, viz., (i) the efficient reactivity and enantiotopic selectivity similar to or higher than those of 2 and (ii) the ready availability of the esters 6 having a suitably functionalized acyl moiety from the corresponding carboxylic acids and their applicability to the enzymatic reactions. These findings have opened a new possibility of the lipase-catalyzed reactions. In this review, several examples are introduced along with some related recent progress on the lipase-catalyzed asymmetric syntheses. The topics include (i) the enantioselective desymmetrization of prochiral 2, 2-disubstituted 1, 3-propanediols using 1-ethoxyvinyl 2-furoate 6b, (ii) the lipase-catalyzed domino reactions using suitably functionalized acyl donors 6e-i for the direct preparation of optically enriched cyclic compounds having multi stereogenic carbon centers, (iii) the dynamic kinetic resolution (DKR) of racemic secondary alcohols by the combined use of lipases and the ruthenium complexes 36a-g, and (iv) the DKR of racemic allylic alcohols (44, 45) by the combination of lipases and the vanadium compound 43. Application of these reactions to the asymmetric total synthesis of natural products is also described.

著者

安藤 能久

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.20, no.11, pp.1033-1040, 1962-11-01 (Released:2010-06-28)

参考文献数

28

著者

小方 芳郎

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.19, no.6, pp.438-448, 1961-06-01 (Released:2010-10-20)

参考文献数

108

被引用文献数

2

著者

周東 智 福岡 正哲 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.58, no.12, pp.1144-1154, 2000-12-01 (Released:2010-01-22)

参考文献数

20

被引用文献数

1 3

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Cyclic ADP-ribose (cADPR, 1) is a newly discovered general mediator involved in Ca2+ signaling. The synthesis of cADPR analogs has been extensively studied by enzymatic and chemo-enzymatic methods using ADP-ribosylcyclase, due to their biological importance. ADP-ribosylcyclase from Aplysia Californica mediates the intramolecular ribosylation of NAD+ and some modified NAD+, which are prepared chemically or enzymatically, at the N-1-position of the purine moiety to yield cADPR or the corresponding analogs. However, the analogs that can be obtained by this method are limited due to the substrate-specificity of the enzyme. We developed an efficient method for the chemical synthesis of cADPR analogs and synthesized cyclic ADP-carbocyclicribose (cADPcR, 2) and its inosine congener (3, cIDPcR) as stable mimics of cADPR, in which an oxygen atom in the ribose ring of cADPR is replaced by a methylene group. Biological activities of cADPR and its analogs were also described.

著者

君嶋 葵

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.78, no.9, pp.901-903, 2020-09-01 (Released:2020-09-10)

参考文献数

8

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Hippolachnin is a polyketide natural product isolated from the marine sponge Hippospongia lachnein in China 2013, which has shown highly potent antibacterial activities against several pathogenic fungi. It features a highly substituted cyclobutane, six contiguous stereocenters, one of which is quaternary carbon and bears an unusual array of four ethyl groups on its convex face. In this review, total syntheses of hippolachnin by four groups are described.

著者

大西 肇

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.5, pp.466-467, 1983-05-01 (Released:2009-11-13)

著者

岩井 清明

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.41, no.11, pp.1110, 1983

著者

早川 謙二 兼松 顕

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.2, pp.109-117, 1986-02-01 (Released:2009-11-13)

参考文献数

58

被引用文献数

6 7

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This article reviews the recent advances in the intramolecular Diels-Alder reactions of furans, which include the reactions with furan as a diene (type I), furan as a part of diene (type II), and furan as a dienophile (type III). This review involves the analysis of the important controlling factors in these reactions as well as their application to the natural product synthesis.

著者

川合 恭平 鈴木 汎

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.37, no.6, pp.494-500, 1979

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We, Toagosei Chemical Industry, have buckled down seriously to the safety problem with making the best use of our experience of plant accidents happened in the past.<BR>With an explosion accident in 1952 as a momentum, our plant operation was standardized. Then, with an explosion accident in 1972 as a momentum, an expert committee for the prevention of plant accidents was institutionalized.<BR>By the said committee, the checking for causes of accidents is done as to each stage of research, engineering, and test operation. The check list is used for this purpose. Now, we would introduce the part relating to the explosion.<BR>Differential Scanning Calorimeter is effective for the checking against explosive chemicals of which counterplan is difficult to be set.

著者

大橋 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.58, no.4, pp.334-338, 2000-04-01 (Released:2009-11-13)

被引用文献数

1

著者

岩井 清明

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.1110, 1983-11-01 (Released:2009-11-13)

著者

長沢 正雄

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.22, no.3, pp.170-176, 1964-03-01 (Released:2010-06-28)

参考文献数

15

著者

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.50, no.12, pp.1131-1139, 1992-12-01 (Released:2009-11-16)

参考文献数

26

被引用文献数

8 8

---

Homogeneous catalysis using chiral metal complexes provides a general principle for chemical multiplication of chirality. A wide range of optically active substances can be synthesized catalytically by the appropriate combination of transition metals or main group elements and suitably designed chiral organic elements. This chemistry is useful not only for stereoselective preparation of chiral compounds in laboratories but also even on industrial level. The recent progress in this field greatly raised the potential of organic synthesis in general. The current status is discussed.

著者

渡嘉敷 通秀

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.43, no.7, pp.703-716, 1985-07-01 (Released:2009-11-13)

参考文献数

69

被引用文献数

2 2

---

Mineral oils are made by refining crude oils with physical operations. On the other hand, synthetic oils are products made by combining low molecular weight components from mineral oil or natural oils and fats via various chemical processes.Those are classified into several categories such as synthetic hydrocarbons (α-olefin oligomer, alkylbenzene, etc.), esters (diester, polyol lester, phosphate, silicate, etc.), ethers (polyalkyleneglycol, polyphenylether) and others (silicone, fluorinated compounds, etc.). Some synthetic fluids show better properties in which mineral oils are poor ; for examples, in viscosity-temperature relations, low tempreature fluidities, high temperature stabilities, fire resistances, etc.Recently, these synthetic oils are getting more important in connection with energy conservation or development of high performance machines. They are applied mainly to aircraft gas turbine oils, automotive engine oils, hydraulic oils, compressor oils and gear oils.In this review, synthetic lubricating oils are introduced for research chemists and chemical engineers of organic syntheses.

著者

小林 淳一 津田 正史

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.55, no.12, pp.1114-1123, 1997-12-01 (Released:2009-11-16)

参考文献数

37

被引用文献数

4 7

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Manzamines, β-carboline alkaloids having unique heterocyclic systems from marine sponges, are of considerable current interest as compounds generated through unprecedented biosynthetic path or as a challenging target for total synthesis. Recently many manzamine-related alkaloids have been isolated from marine sponges, indicating the unique biogenetic path of manzamines.

著者

北 将樹

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.4, pp.371-373, 2019-04-01 (Released:2019-04-08)

著者

北川 敏一 竹内 賢一 小松 紘一 木下 知己

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.8, pp.746-757, 1992-08-01 (Released:2009-11-16)

参考文献数

44

被引用文献数

2 3

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Two novel classes of hydrocarbons, i.e. hydrocarbon salts and ionically dissociative covalent hydrocarbons, were prepared from Kuhn's carbanion (5-) and various cyclopropenylium and tropylium ions.The ionic structures of the hydrocarbon salts were evidenced by IR spectra (solid state), UV-vis spectra (DMSO), and electric conductivity measurements (DMSO) The salt obtained from 5- and tricyclopropylcyclopropenylium ion formed a unique covalent compound in chloroform which can exist only in solution. The salt of 5- and tricyclopropyltropylium ion was found to undergo both coordination and single-electron transfer in THF, affording a yet unknown type of equilibrium system, in which the ionic, radical, and covalent species coexist.Studies on the free energies of heterolysis of the newly synthesized covalent hydrocarbons revealed the importance of the steric effect in the heterolytic cleavage of σ carbon-carbon a bond. It was also found that a slight difference in the cation stability differentiates the product, either ionic or covalent, of the reaction with a carbanion.

著者

大村 智

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.392-393, 2000-05-01

参考文献数

5

著者

熊本 卓哉 石川 勉 大村 智

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.1, pp.49-58, 2004-01-01

参考文献数

39

被引用文献数

15

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Kinamycin antibiotics, strongly active against gram-positive bacteria, were isolated from the culture broth of <I>Streptomyces murayamaensis</I>. Their structures were firstly determined to be a benzo [<I>b</I>] carbazoloquinone skeleton with <I>N</I>-cyanamide [N-C&equiv;N] moiety. After that, prekinamycin was isolated from the same organism as a biosynthetic precursor and the same 6-6-5-6 ring system was also proposed for the structure. But problems still remained on the determination of substituent pattern at <I>N</I>-cyanamide moiety by spectroscopic means. Recently, the structures of kinamycins and prekinamycin were revised to be a benzo [<I>b</I>] fluorene skeleton with diazoalkane moiety [C<SUP>-</SUP>-N<SUP>+</SUP>&equiv;N]. However, a synthetic compound with the revised structure for prekinamycin was found to be different from natural prekinamycin, instead an isomeric benzo [<I>a</I>] fluorene skeleton, a 6-5-6-6 ring system was proposed for the natural product, which was newly named as isoprekinamycin. Herein the chemistry of kinamycins and their related compounds with structural confusions is reviewed, especially focused on the history of structural determination and recent synthetic studies.

著者

砂塚 敏明 長光 亨 大村 智

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.56, no.6, pp.478-488, 1998-06-01

参考文献数

37

被引用文献数

2

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The first total synthesis of the microbial a-pyrone meroterpenoid, (+) -pyripyropene A (1), acyl-CoA : cholesterol acyltransferase (ACAT) inhibitor, which is effective and concise convergent approach (14 steps, 9.3% overall yield), designed to afford easy access to both the natural products and a variety of analogs, has been achieved. The key step is the coupling reaction between a-pyronepyridine moiety (4) and the acid chloride of sesquiterpene moiety (3) in the presence of Lewis acid to construct ketone (2). The sesquiterpene moiety has been synthesized started from (+) -Wieland-Miescher ketons via stereoselective reductive formylation, palladium associated carbonylation, and allylic oxidation.<BR>(+) -Pyripyropene E (36) also has been synthesized from farnesyl acetate (9 steps, 9.6% overall yield). The convergent and stereoselective route exploited a biomimetic polyene cyclization as the key transformation.