巻号一覧
65 巻, 4 号
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佐竹 彰治2007 年 65 巻 4 号 p. 298-307
発行日: 2007/04/01
公開日: 2010/10/20
ジャーナル フリーFunctionalization and multiplication of porphyrins by transition metal-mediated reactions (Sonogashira coupling, Negishi coupling, Stille coupling, Mizoroki-Heck alkenylation, Buchwald-Hartwig reaction, Suzuki-Miyaura coupling, cobalt-mediated [2+2+2] cyclization, Grubbs' metathesis reaction, etc.) are reviewed. When the above reactions are applied to porphyrins, diluted conditions (typically 110 mM) are used due to low solubility. As the dilution, relatively large amounts of metal species are used due to decreasing of turn over numbers of the catalysts. Copper reagent is excluded when free base porphyrins are treated without protection. In multiplication of porphyrins by simultaneous multiple metal-mediated couplings, each yield and existence of side-products greatly affect isolation of the target material. In this review, modified conditions and side-reactions are presented to let know the problems to chemists who synthesizes functional porphyrins and develops metal-mediated reactions.抄録全体を表示PDF形式でダウンロード (1704K) -
古川 喜朗, 鈴木 利雄, 三上 雅史, 北折 和洋, 吉本 寛2007 年 65 巻 4 号 p. 308-319
発行日: 2007/04/01
公開日: 2010/10/20
ジャーナル フリーAs optically active compounds are playing important roles in a living body as diverse components of bioactive materials, they are mainly utilized in the pharmaceutical field. Going with the stream of the huge advance in chiral technology, we have developed the industrial process to produce optically active propanols by stereoselective assimilation of racemic ones with microorganisms. In addition to that, we have industrialized the technology of hydrolytic kinetic resolution catalyzed by chiral salen complex to prepare optically active epichlorohydrin, and expanded our technical field. Furthermore, we have tried to spread our series of optically active C 3 and C 4 compounds derived from such propanol derivatives. In this paper, investigation of the industrial process for not only the optically active basic chiral propanol derivatives but also chiral building blocks and pharmaceutical intermediates will be discussed, combining our efforts to prevent racemization in the reaction and so on.抄録全体を表示PDF形式でダウンロード (1918K) -
太田 公規, 遠藤 泰之2007 年 65 巻 4 号 p. 320-333
発行日: 2007/04/01
公開日: 2010/10/20
ジャーナル フリーThe icosahedral boron cluster : dicarba-closo-dodecaboranes (carboranes) are chemical building blocks of high boron content, remarkable chemical stability, spherical geometry and hydrophobic molecular surface. These features of carboranes may allow wide variety of application for molecular construction, medicinal chemistry and materials sciences. However, little attention has been paid to the understanding their nature in view of synthetic organic chemistry. We have aimed to understand their electronic property, reactivity and to apply their spherical geometry for design and synthesis of biologically active molecules and three-dimensional structures. In this review, we describe development of synthetic methods on the carborane cage, evaluation of the characteristic electronic effects and steric effects of carborane, molecular construction based on spatial definition by carborane and evaluation and application of the hydrogen-bonding affinity of carboranes.抄録全体を表示PDF形式でダウンロード (2134K) -
野村 信嘉, 鶴来 交, 吉田 奈央, 小宮山 晋, 岡田 鉦彦2007 年 65 巻 4 号 p. 334-346
発行日: 2007/04/01
公開日: 2010/10/20
ジャーナル フリーThe Tsuji-Trost reaction (TTR) has been one of the central topics in organic synthesis since its discovery. In spite of its spectacular success in organic synthesis, the typical reaction had not been utilized in polymer synthesis. Its uniqueness and effectiveness prompted us to develop the polymerization via TTR. Our examination of the reaction conditions revealed that 1, 4- bis (diphenylphosphino) butane (dppb) as a ligand and N, O-bis (trimethylsilyl) acetamide as a base were important. Degrees of polymerization in the polycondensation highly depend on the stoichiometric balance of the two monomers according to the Carothers-Flory equation. However, we found that the degrees of polymerization did not always depend on the stoichiometric balance of the monomers when the reaction pathways were controlled by catalysis. About sixty years later Carothers-Flory established the experimental and theoretical principles of homogeneous polycondensations, the highly controlled catalysis made a way to deviate the stoichiometric restriction in the polycondensation.抄録全体を表示PDF形式でダウンロード (2111K) -
鈴木 教之2007 年 65 巻 4 号 p. 347-357
発行日: 2007/04/01
公開日: 2010/10/20
ジャーナル フリーIt is generally known that small cyclic alkynes such as cyclopentyne is extremely reactive and unstable. Therefore it has been believed impossible to isolate cyclopentyne compounds.
We recently reported that low-valent group 4 metallocenes reacted with 1, 2, 3-butatrienes to give 1-metallacyclopent-3-yne complexes and that resulted compounds are surprisingly stable and isolable. We succeeded in determination of their molecular structures by X-ray diffraction analyses, and showed that these are five-membered cyclic alkynes, while π, π-interaction of butatriene was also suggested. In this review, the preparation, structure and reactivity of these 1-metallacyclopent-3-yne compounds are described.
The 1-zirconacyclopent-3-yne complexes reacted with another 'zirconocene' to form bimetallic complexes in which the cyclic alkyne coordinated to the other zirconocene moiety, indicating that the zirconacyclopentyne behaved as an alkyne. Seven-membered cyclic alkynes were also prepared from 1, 2, 3-butatriene and a zirconocene-alkyne compound. Protonolysis and subsequent nucleophilic attack to aldehyde gave allenyl or dienyl alcohol depending on proton source.抄録全体を表示PDF形式でダウンロード (1609K) -
井上 宗宣, 横田 和加子, 加藤 正2007 年 65 巻 4 号 p. 358-369
発行日: 2007/04/01
公開日: 2010/10/20
ジャーナル フリーScyphostatin, isolated from the culture broth of Trichopeziza mollissima SANK 13892 in 1997, is a powerful and specific inhibitor of neutral sphingomyelinase (N-SMase) and is believed to be a promising new lead for the treatment of AIDS, inflammation, and immunological and neurological disorders. Structurally, this natural product features a novel, highly oxygenated cyclohexane ring incorporated with a C-20 unsaturated fatty acid-substituted amino propanol side chain. In this article, we wish to disclose the whole story of our successful total synthesis of naturally occurring (+) -scyphostatin. In the initial chapter, the first-generation strategy for the enantioselective synthesis of the epoxycyclohexenone part has been described. Subsequently, the second-generation strategy, which led to the first total synthesis of (+) -scyphostatin, has been presented. In the last chapter, the synthesis of several scyphostatin analogues to study the structure-activity relationship has been mentioned briefly.抄録全体を表示PDF形式でダウンロード (1825K) -
本城 崇2007 年 65 巻 4 号 p. 370-371
発行日: 2007/04/01
公開日: 2010/10/20
ジャーナル フリーThe discovery of stable carbenes in the last decade of the 20th century has brought about extensive research on the chemistry of N-heterocyclic carbenes. Recently the powerful catalytic activity of N-heterocyclic carbenes has been demonstrated by new organocatalytic transformations. This review focuses on the asymmetric benzoin reactions catalyzed by N-heterocyclic carbenes. Chiral nucleophilic carbenes catalyze the benzoin condensation in good yields and exellent enantioselectivities.抄録全体を表示PDF形式でダウンロード (308K) -
金井 求2007 年 65 巻 4 号 p. 372-378
発行日: 2007/04/01
公開日: 2010/10/20
ジャーナル フリーPDF形式でダウンロード (2437K) -
大野 桂二, 佐藤 睦2007 年 65 巻 4 号 p. 379-381
発行日: 2007/04/01
公開日: 2010/10/20
ジャーナル フリーPDF形式でダウンロード (368K) -
佐竹 彰治, 遠藤 泰之, 野村 信嘉, 加藤 正2007 年 65 巻 4 号 p. 382
発行日: 2007/04/01
公開日: 2010/10/20
ジャーナル フリーPDF形式でダウンロード (188K)
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