有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
73 巻 , 3 号
選択された号の論文の9件中1~9を表示しています
巻頭言
総説および総合論文
  • 田中 隆行, 大須賀 篤弘
    2015 年 73 巻 3 号 p. 220-229
    発行日: 2015年
    公開日: 2015/04/21
    ジャーナル 認証あり
    meso-meso, β-β, β-β Triply linked porphyrin arrays (porphyrin tapes) have been extensively studied in the last decade owing to their remarkable physical properties such as extremely red-shifted absorption bands reaching up to IR region and large two-photon absorption cross-sections. Recently, hybrid porphyrin tapes have emerged as novel promising molecular motifs by realizing ample chemical stabilities and good solubilities in common organic solvents. Synthesis of porphyrin-hexaphyrin hybrid tape has been also achieved and the unique property has been revealed.  In other cases, various aromatic segments have been fused onto the porphyrin or hexaphyrin periphery to create fused porphyrinoids. These novel fused porphyrinoids are promising molecules as near-infrared(NIR)-absorbing dyes, pointing to future applications such as conducting wire, NIR emitter, photovoltaics, and nonlinear optical materials.
  • 橋本 勝, 村上 貴宣
    2015 年 73 巻 3 号 p. 230-240
    発行日: 2015年
    公開日: 2015/04/21
    ジャーナル 認証あり
    In the course of our mechanistic studies of mycoparasitism between Lambertella spp. (the parasite) and Monilinia fructigena (M. f., the host) on apple fruits, we isolated known lambertellin (1) and new spirobutenolides lambertellols A (2), B (3). Lambertellols were detected only when the host M. f. co-inhabited in the broth of M. f. Lambertellols 2, 3 were readily interconverted and gradually decomposed into 1. Our total syntheses enable the SAR studies to disclose that 1 should be the real active species and 2 and 3 are diffusible precursors. In order to rationally explain these observations, we performed dynamic analyses of the metabolites to disclose a novel alleropathy ‘Lambertellin system’ as described in this article. This mechanism also accords with the progress of ‘Natsu-Nenju’ disease on apple fruits, which is known to be a mysterious phyto-disease because of two unique stages of its lifecycle, anamorphic (asexual) and teleomorphic (sexual). Only organic chemistry based investigations could approach the final conclusion in this particular case.
  • 金 鉄男
    2015 年 73 巻 3 号 p. 241-253
    発行日: 2015年
    公開日: 2015/04/21
    ジャーナル 認証あり
    Functional fullerenes have been used widely as excellent n-type semiconductors in solution processable organic electronics, especially as the unique electron acceptors for organic photovoltaics due to their significant increase in solubility while preserving certain electronic and optical properties of pristine fullerenes. Numerous efforts have been made to develop new fullerene functionalization. In comparison with the traditional methods, such as nucleophilic addition of organometallic reagents, cycloaddition, and addition of free radicals, the transition-metal-catalyzed fullerene functionalization has been proved to exhibit high efficiency and selectivity under mild reaction conditions as well as a high compatibility with a wide range of functional groups. We have been interested in the catalytic generation and reactivity of the fullerene radicals. The account describes our recent achievements for the synthesis of various monosubstituted hydrofullerenes, fullerene cycloadducts, single-bonded fullerene dimers, and amine-substituted 1,4-bisadducts in the presence of cobalt and copper catalysts via the formation of the fullerene monoradical as an active species.
  • 有澤 光弘, 西田 篤司, 周東 智
    2015 年 73 巻 3 号 p. 254-265
    発行日: 2015年
    公開日: 2015/04/21
    ジャーナル 認証あり
    We have established aromatic enamide-ene metathesis to give highly substituted indole derivatives. This is a new method for the preparation of chiral 2-trans-cyclopropyl indoles, which successfully led to our H4 antagonist candidates. Based on this findings, we also designed and synthesized conformationally restricted analogues and regioisomers of the nonsteroidal anti-inflammatory drug indomethacin. Evaluation of the inhibitory effects of these compounds on COX, P-glycoprotein, and multidrug-resistance indicated that NSAIDS modulation of multidrug resistant P-glycoprotein and multidrug-resistant protein-1 is not associated with COX-1 and COX-2 inhibitory activities.
  • 道田 誠, 今井 誠
    2015 年 73 巻 3 号 p. 266-275
    発行日: 2015年
    公開日: 2015/04/21
    ジャーナル 認証あり
    A process development research of renin inhibitor 1 for anti-hypertensive drug candidate is described. This compound consists of three intermediates, and especially the key intermediate is chiral lactone 3 which contains three asymmetric carbons. We developed two different approaches to construct those carbons for the synthesis of the common intermediate 9. Namely, scalable synthetic method was established from d-glucose, and 6 kg of 1 was provided for early clinical studies. Then we also developed a highly efficient alternative synthetic method of 1 for manufacturing from n-butyryl chloride 24 by using Evans stereoselective alkylation, followed by stereoselective bromolactonization as key reactions.
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