著者

平間 正博

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.418-431, 1983-05-01 (Released:2009-11-13)

参考文献数

40

被引用文献数

2 3

---

Convergent and enantiospecific syntheses of compactin (1 a) and mevinolin (1 b), potent competitive inhibitor of HMG-CoA reductase, have been achieved via asymmetric intramolecular Diels-Alder reaction of acyclic (E, E, E) -trienone 4 leading to trans-octalone 3, a common intermediate for congeners. Chirality of C13 in 4 was designed to induce the four asymmetric centers with desired configuration by this reaction : the chirality controlled the approach of the dienophile from a single diastereotopic face. Trienone 4 was expeditiously constructed by the combination of two segments 5 and 6. Enantio- and stereo-specific synthesis of 6, a chiral 1, 3, 5- triol derivative, rested on the two novel methodologies, i.e, the convenient asymmetric reduction of β-keto carboxylate 19 d with baker's yeast and the regio- and stereo-selective iodofunctionalization (1, 3-asymmetric induction) of homoallylic carbamate. Preparation of 5 in its optically active form was accomplished by the elaboration of readily available γ-lactone 12.

著者

今西 武 花岡 美代次

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.403-417, 1983-05-01 (Released:2010-01-22)

参考文献数

64

被引用文献数

1 3

---

This article describes our recent synthetic studies on some kinds of alkaloids, which possess various carbon substituted piperidine parts in their structures, starting from a common synthon, N-substituted 1, 6-dihydro-3(2H)-pyridinone. Syntheses of catharanthine, ibogamine, epiibogamine, tabersonine, cleavamine, eburnamonine, corynantheidol, quinine, and tecomanine are involved.

著者

本間 千裕 加納 太一

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.80, no.2, pp.92-102, 2022-02-01 (Released:2022-02-09)

参考文献数

94

---

Chiral amine catalysts are widely utilized in various asymmetric reactions. Among them, binaphthyl-based secondary amine catalysts show unique reactivity and unusual stereoselectivity in comparison with frequently used ʟ-proline and its derivatives. In spite of their utility, however, asymmetric reactions employing binaphthyl-based amines are rare because of their synthetic inefficiency. In this context, we have developed chiral secondary amine catalysts based on a phenylcyclopropane scaffold as a novel chiral motif. Newly synthesized amine catalysts function as effective catalysts for several asymmetric reactions. In addition, the phenylcyclopropane-based amino sulfonamide was found to be an effective catalyst for the syn-selective Mannich reaction and conjugate addition with alkynyl Z-ketimines.

著者

河野 一通 河西 政次

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.48, no.9, pp.824-833, 1990-09-01 (Released:2010-01-22)

参考文献数

41

被引用文献数

1 5

---

The studies on the chemistry of mitomycins are described : i) identification and structural elucidation of mitomycins D, E, F, G, I, J, K, L, M, albomitomycin A, and isomitomycin A from the fermentation broth; ii) derivation of mitomycins structurally close to naturally occurring mitomycins; iii) mitomycin rearrangement, the interconversion between mitomycin A, albomitomycin A, and isomitomycin A;iv) chemical con-version of isomitomycin A from mitomycin A; v) 3α-alkoxymitomycins, unexpected by-products in decarbamoylation of mitomycins;vi) the configuration of mitiromycin.

著者

伊藤 芳雄 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.47, no.7, pp.606-618, 1989-07-01 (Released:2009-11-13)

参考文献数

56

被引用文献数

17 19

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The 1β-methylcarbapenem antibiotics represented by 3, 4, and 5, have been the focus of current synthetic endeavor due to prominent antibacterial activities and broad spectra as well as enhanced chemical and metabolic stability. Progress of the syntheses of 1β-methylcarbapenem key intermediates represented by 6, are reviewed based on the synthetic methods of the characteristic 1β-methyl substituent involved in the contiguous four chiral centers of 6.

著者

福井 三郎 田中 渥夫

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.41, no.5, pp.384-394, 1983-05-01 (Released:2009-11-13)

参考文献数

80

被引用文献数

5 5

---

Enzymes, which catalyze a variety of reactions in living systems, have many specific features, such as regiospecificity, stereospecificity and substrate specificity. Furthermore, such reactions can be carried out under very mild conditions. Immobilization of biocatalysts (enzymes, and enzymecontaining organelles, microbial cells and other living systems) is attracting worldwide attention, because immobilized biocatalysts catalyze biochemical reactions under more stabilized conditions than their free counterparts and, moreover, they can be reused economically. At present, applications of immobilized biocatalysts include (a) production of useful compounds by stereospecific and/ or regiospecific reactions under mild conditions, (b) production of energy by biological processes, (c) analyses of various compounds with high sensitivity and high specificity, and (d) utilization in medical fields such as new types of drugs and artificial organs etc.This review deals with the several examples of immobilized biocatalysts applied to biosynthesis and bioconversion of organic compounds. Utilization of immobilized biocatalysts in the presence of organic solvents is also described.

著者

小林 秀彦

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.41, no.4, pp.371-372, 1983-04-01 (Released:2009-11-13)

被引用文献数

1 1

著者

出雲崎 昇

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.4, pp.369-370, 1983-04-01 (Released:2009-11-13)

著者

吉井 英一 武田 敬

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.4, pp.348-358, 1983-04-01 (Released:2009-11-13)

参考文献数

90

被引用文献数

2 2

---

Recent progress in the total syntheses of naturally occurring di- and tricyclopentanoid sesquiterpenes is reviewed, placing particular emphasis on the methodology for the construction of the skeletons and further on the total synthesis of quadrone.

著者

小谷野 喬

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.42, no.3, pp.252, 1984-03-01 (Released:2009-11-13)

著者

林 輝幸

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.3, pp.239-250, 1983-03-01 (Released:2009-11-13)

参考文献数

165

被引用文献数

1 1

---

Effects of the structure of diphosphines, especially of n in Ph2P (CH2) nPPh2 (PnP), on the structure, reactivity, catalytic activity and selectivity, and asymmetric induction ability of transition metal complexes are described. The catalytic activity and selectivity change variously depend on n when PnP are used with catalyst metal complexes. P2P is suitable when chelating species is active, while P3P or P4P is superior when dissociation of the diphosphine is necessary. In asymmetric reactions, the diphosphines which form rigid coordination structure bring about high optical yield.

著者

橋本 俊一 戸田 正明

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.3, pp.221-238, 1983-03-01 (Released:2009-11-13)

参考文献数

73

被引用文献数

2 2

---

The recent discovery of the new family of compounds, named leukotrienes because of their origin from leukocytes and a structural characteristic, the conjugated triene, has significantly increased our knowledge of arachidonic acid metabolism.This review will focus on the chemistry leading to the complete stereochemical elucidation of the leukotrienes, as well as more recent synthetic advances.

著者

中筋 一弘 中塚 正勝 村田 一郎

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.41, no.3, pp.204-220, 1983-03-01 (Released:2010-01-22)

参考文献数

136

被引用文献数

5 6

---

According to a system of classification for multi-stage redox systems proposed by Hünig, tetrathiafulvalene (TTF), bithiopyranylidene (BTP) are considered to be Weitz-type donors whereas tetracyanoquinodimethane (TCNQ) is regarded as Wurster-type acceptor. Recent efforts to explore new redox systems have provided various structural modifications, such as symmetrical, unsymmetrical, condensed, and inserted versions on TTF, BTP, and TCNE. In this review recent progress in design and synthesis of the modified TTF, BTP, and TCNE systems is described.

著者

矢坂 正大

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.2, pp.190-191, 1983-02-01 (Released:2009-11-13)

著者

平田 文雄

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.2, pp.178-185, 1983-02-01 (Released:2009-11-13)

参考文献数

18

---

The current status of prostaglandin research is reviewed mainly on the primary prostaglandins, widely distributed in the living body, and on prostaglandin analogues having more stable structure and higher selective biological activities, which were developed by reference to the structures and activities of the primary PGs. Especially, recent aspect on their clinical application and development is explained. Moreover, the new field is viewed mainly on the future commercialization of PGI2 and TXA2 synthesis inhibitor, which will be applied mainly on circulatory system, from Yin-Yang theory. Further, recent rapid progress in leukotriene research on lipoxygenase system in arachidonic acid cascade will also been mentioned.

著者

山田 靜之 木越 英夫

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.53, no.1, pp.13-21, 1995-01-01

参考文献数

22

---

Synthetic studies on the bracken ultimate carcinogen (3) and its artificial analogues (32, 33) are described. The synthesis of (-) -ptaquilosin (2) the aglycon of a potent carcinogen ptaquiloside (1) from bracken and its (+) - enantiomer (<I>ent</I>- 2) was achieved starting with (+) -dimenthyl (1<I>R</I>, 2<I>R</I>) -cyclopentane-1, 2-dicarboxylate. Dehydration of ptaquilosin (2) under weakly basic conditions led to the ultimate carcinogen (3). DNA cleaving activities of both enantiomers (3) were compared, the one (3) derived from natural (-) -ptaquilosin (2) being more efficient. Reactivities of the ultimate carcinogen (3) toward DNA are described. DNA was shown to be alkylated at the particular sites of purine bases and to undergo cleavage. The molecular mechanism of DNA cleavage with the ultimate carcinogen (3) was disclosed using deoxytetranucleotide d (GTAC) as a model DNA substrate.

著者

小島 秀子 松浦 輝男

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.56, no.4, pp.268-279, 1998-04-01 (Released:2009-11-16)

参考文献数

59

被引用文献数

28 35

---

Chiral crystallization of optically inactive (achiral) compounds such as benzophenone, phenol, phenanthrene, etc. has not been a commonly known phenomenon in organic chemistry. These compounds are known to crystallize to chiral crystals from their solutions. This review deals with this phenomenon, describing (1) what is chiral crystallization and how to find organic compounds undergoing chiral crystallization, (2) the preparation of chiral crystals from achiral organic compounds, (3) the characterization of chiral crystals, (4) the crystal structure of chiral crystals and the factors of the generation of chirality, (5) the chiral crystallization of two-component molecular compounds, (6) absolute asymmetric synthesis utilizing chiral crystallization, (7) other applications of chiral crystallization. Part 1 describes chapters (1), (2), (3), and (4).

著者

八木沢 行正

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.30, no.7, pp.654-662, 1972

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発売を許されている抗生物質は, 医薬品76種類 (うち2種類は発売中止), 動物専用7種類, 農業専用5種類の合計88種類である。5年前 [有合化 25 703 (1967)] と較べると, 医薬品にDicloxacillin, Hetacillin, Carbenicillin, Flucloxacillin, Ciclacillin, Cephaloglycin, Cefalexin, Cefazolin, Aminodeoxykanamycin, Gentamicin, Doxycycline, Minocycline, Josalnycin, Clindamycin, Enramycin, Rifampicin, Siccanin, Actinomycin D, Daunorubicin, Bleomycinの20種類が加わり, 動物専用にDestomycin A, Virginiamycin, Macarbomycin, Moehomycin, Thiopeptirの5種類, 農業専用にPolyoxinが加わり, このほか, いくつかの新物質が近く発売されようとしている。

著者

岡 希太郎 原 昭二

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.1, pp.25-39, 1979

被引用文献数

1

---

This review involves the synthetic studies on the salamander alkaloids isolated from an animal venom in the skin gland of Salamandra maculosa <I>Laurenti</I>. Syntheses of three groups of the alkaloids, one with a bicyclo-oxazolidine system, one with a carbinolamine system, and another with a pure 3-aza-A-homo steroid system, are discussed separately. It will be emphasized that the synthetic works described herein made a considerable contribution to the structure analyses of this field of alkaloids and earlier proposed structures based on X-ray and spectroscopic analyses have been changed step by step. Regio and stereospecific syntheses of the alkaloids are mainly discussed in connection with the construction of the bicyclo-oxazolidine system of the major alkaloids and with Beckmann rearrangement of steroid 3-ketoximes for the syntheses of the other alkaloids.

著者

太田 俊作 岡本 正夫

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.41, no.1, pp.38-50, 1983-01-01 (Released:2009-11-13)

参考文献数

71

被引用文献数

7 7

---

Many useful acylation reactions including carbonylation have been improved in yield, reaction condition and manipulation by using 1-acylimidazole. In this review important synthetic applications of 1-acylimidazole after Staab's review in 1962 are described.