著者

浅岡 守夫 武井 尚

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.8, pp.718-727, 1983-08-01 (Released:2009-11-13)

参考文献数

41

被引用文献数

2 3

---

This article describes carbon-carbon bond forming reactions utilizing trialkylsiloxy substituted heterocyclic aromatic compounds and their synthetic applications. Siloxyfurans synthesized from buten-4-olides or succinic anhydrides reacted with dienophiles to give corresponding Diels-Alder adducts. In the presence of Lewis acids they also reacted with orthoesters, acetals, α, β-unsaturated ketones, aldehydes, and ketones to give corresponding buten-4-olide derivatives or bislactones.Similar reactions of siloxyoxazoles synthesized from 2-oxazolin-5-ones are also described.

著者

小林 進

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.8, pp.745-754, 1983-08-01 (Released:2009-11-13)

参考文献数

26

被引用文献数

3 4

---

The reaction of γ, δ- or δ, ε-unsaturated carboxylic acid with halogen afford halolactone in high yield. This halolactonization reaction generally proceeds in a high stereo- and regiospecific manner. This makes the reaction one of the most important procedures for the functionalization of the carbon-carbon double bond.This review provides illustrative examples of the synthesis of natural products where halolactonization reaction plays an important role.Some related reactions are also described.

著者

相原 良平

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.8, pp.778, 1983-08-01 (Released:2009-11-13)

被引用文献数

1 1

著者

渡辺 三明

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.8, pp.728-744, 1983-08-01 (Released:2010-01-22)

参考文献数

156

被引用文献数

5 6

---

Directed metalation has recently been recognized as an efficient new synthetic methodology for the regiospecific construction of highly substituted aromatic systems. In this review, the utility of the directed metalation strategy for the synthesis of a variety of complex aromatic compounds, especially natural products, is described.

著者

厚東 伸佶 森島 直彦 膳昭之 助

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.8, pp.701-717, 1983-08-01 (Released:2009-11-13)

参考文献数

168

被引用文献数

9 10

---

Recent progress in the methods for Ο-glycosylation are reviewed. The topics are summarized in the eleven items : (i) α-Glc type glycosylation, (ii) β -Glc type glycosylation, (iii) α-Man type glycosylation, (iv) β-Man type glycosylation, (v) α-GlcN type glycosylation, (vi) β-GlcN type glycosylation, (vii) 2-deoxy-glycosylation, (viii) ketosylation, (ix) acetal glycosylation (x) the topics relating to ο-glycosylation, and (xi) polysaccharide synthesis.

著者

飯田 英夫 樹林 千尋

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.7, pp.652-666, 1983-07-01 (Released:2010-01-22)

参考文献数

116

被引用文献数

22 20

---

Nitrones are well-known to behave as 1, 3-dipoles and readily undergo thermal [3+2] cycloaddition reactions with olefins to produce isoxazolidine derivatives, which can be converted into β-amino alcohols by subsequent reductive N-O bond cleavage. The synthetically significant features of these reactions are carbon-carbon bond formation and introduction of nitrogen and oxygen functionality with concomitant high siteselectivities, regioselectivities, and stereoselectivities. Although this reaction mode has been alloted a more limited role in organic synthesis, more recent studies have demonstrated its general utility in the synthesis of a wide variety of natural products, particularly alkaloids. It is the purpose of this review to indicate the usefulness and synthetic aspects of nitrone methodology applicable to the natural products synthesis.

著者

辻 二郎

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.7, pp.619-632, 1983-07-01 (Released:2009-11-13)

参考文献数

54

被引用文献数

9 8

---

Following reactions of various allylic compounds catalyzed by palladium-phosphine complexes are surveyed. Allyl carbonates react with nucleophiles under neutral conditions at room temperature. Allyl alkenyl carbonates and allyl β-keto esters undergo decarboxylation and regioselective intramolecular allylation to afford allylated ketones. 1, 3-Dienemonoxides react with nucleophiles to give 1, 4-adduct with high selectivity. Palladium-catalyzed cyclization of methyl (E) - 3-oxo-8-phenoxy-6-octenoate gives 3-vinylcyclopentanone-2-carboxylate, which is useful starting material for steroids and jasmonate syntheses. Allyl alkenyl carbonates and allyl β-keto esters are converted to α, β-unsaturated ketones by decarboxylative dehydrogenation in acetonitrile using diphosphine. Allylic compounds are converted to mainly 1-olefins by hydrogenolysis with formates. Allyl carbonates are carbonylated under mild conditions to give β, γ-unsaturated esters. Conjugated dienes are formed from allylic compounds by palladium- catalyzed elimination reaction.

著者

大城 芳樹 平尾 俊一

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.41, no.7, pp.604-618, 1983-07-01 (Released:2009-11-13)

参考文献数

82

被引用文献数

3 4

---

Palladium catalyzed or promoted reactions provide a versatile and selective method for the synthesis of heterocyclic compounds. The role of palladium complexes in the synthesis of N-heterocycles is surveyed.

著者

古舘 信生

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.439-450, 1983-05-01 (Released:2009-11-13)

参考文献数

66

被引用文献数

1

---

Various organic compounds for conventional color photography by chromogenic development are reviewed.Compounds concerned with the dynamic processes of color development, i.e., color forming coupler, colored coupler, development inhibitor releasing (DIR) compounds and quinone-diimine scavenger, and with the static properties of color image such as hue and dye stability, are briefly described.

著者

岡野 多門 吉田 壽勝

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.359-364, 1983-04-01 (Released:2009-11-13)

参考文献数

27

被引用文献数

7 7

---

Three types of Rh (I) hydridotrialkylphosphine compounds, trans-RhH(N2) L2(L=P(t-Bu)3, PPh(t-Bu)2, PCy3, P(i-Pr)3), Rh2H2(μ-N2)L4(L=PCy3, P(i-Pr)3), and RhHLn(n=3, L=P (i-Pr)3, PEt3 ; n=4, L=PEt3), were prepared by reducing RhCl3·3 H2O with Na/Hg in THF. They were proved to be extremely strong nucleophiles and serve as efficient catalysts for hydrogenation of nitriles, ketones, and alkynes, and H-D exchange reaction of H2 and H-C(sp2, sp3)bond with D20 through activation of H2 and water, respectively. They also catalyze the hydrogenation of carbonyl and nitro compounds with H2O-CO and the hydroformylation of olefins with formaldehyde.

著者

杉 義弘

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.6, pp.577-587, 1983-06-01 (Released:2009-11-13)

参考文献数

83

---

The recent advances in the homologation of methanol have been reviewed. The effects of iodine, phosphines, and co-catalysts on the cobalt catalyzed reaction are discussed. Methanol activation is enhanced by the addition of iodine through the formation of methyl iodide. Phosphine modification improves the selectivity of ethanol. The synergy is observed between cobalt and co-catalysts, such as ruthenium and iron. The addition of these co-catalysts improves the rate and the selectivity of ethanol. Transition metal complexes of iron, rhodium, ruthenium, and manganese catalyze the homologation of methanol in methanol amine solution. Carbon dioxide is produced as the oxygenated by-product in the place of water. The synergy between iron and manganese carbonyls enhances the rate and the selectivity of ethanol. The mechanistic aspects are also discussed.

著者

紫垣 明典

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.6, pp.553-560, 1983-06-01 (Released:2009-11-13)

参考文献数

15

---

Acetic acid, an important chemical intermediate, is produced commercially by one of three routes, acetaldehyde oxidation, liquid-phase hydrocarbon oxidation, and methanol carbonylation. Among them, the low pressure carbonylation of methanol, developed by Monsanto Co., has been highly appreciated in view of bright success of C1 chemistry. The history of acetic acid industry is reviewed, and the progress of acetic acid manufacturing technology is discussed.

著者

縄田 伍七 宮崎 晴彦

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.6, pp.545-552, 1983-06-01 (Released:2009-11-13)

参考文献数

109

被引用文献数

1 2

---

Various routes of ethylene glycol synthesis from one-carbon raw materials are reviewed. Recent advances and interesting developments in the direct synthesis from synthesis gas, the two-step process comprising oxidative coupling of CO to oxalates followed by hydrogenation, formaldehydebased routes via glycolic acid esters, hydroformylation of formaldehyde, reaction of methanol with formaldehyde and methanol coupling reactions are summarized.

著者

小野 田武 和田 啓輔

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.6, pp.515-523, 1983-06-01 (Released:2009-11-13)

参考文献数

17

---

The growing scope of homogeneous metal catalyst in C1 chemistry is briefly reviewed. The matal catalyzed C1 reactions, important from industrical point of views, are classified, first, into several groups, in words of the starting material or the reaction pattern. Then, the relationships, between the elemental reaction path and the characteristic feature of the metal center, are discussed. Finally, some comments are added for application of the homogeneous catalyst to the actual commercial plant.

著者

岩隈 建男 山田 幸一郎 武田 幹男

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.41, no.5, pp.451-456, 1983-05-01 (Released:2009-11-13)

参考文献数

27

被引用文献数

1 2

---

Asymmetric reduction of prochiral cyclic imines with chiral sodium acyloxyborohydrides (5 a-i), which are easily prepared by the reaction of NaBH4 with various N-acyl α-amino acids, has been investigated. Of these new reducing agents, triacyloxyborohydrides (5 c-f), derived from NaBH4 (1 eq.) and (S)-N-acylproline (3 eq.), were found to reduce 3, 4-dihydropapaverine (1) in tetrahydrofuran to (S)-norlaudanosine (2) in 60 % optical yield. The N-benzyloxycarbonyl derivative (5 c) could be isolated as a powder and characterized. The effect of solvents on this asymmetric reduction has been examined by the use of the isolated reagent (5 c) halogenated alkane solvents such as CH2Cl2 or CHCl2CH3 gave a better optical yield of compound (2) (70 % e. e.). The reagent (5 c); also reduced other cyclic imines (6 a-c) and (8) to the corresponding alkaloids (7 a-c) and (9) in excellent optical yields (70-86 % e. e.), providing an effective route to the asymmetric synthesis of these alkaloids. The asymmetric reduction of the imines (10 and 13) also proceeded smoothly to furnish the compounds (11 and 14), the precursors of TMQ and TA-073 (bronchodilating agents), in high optical yields. A possible reaction path for this reduction is also presented.

著者

河野 一通 河西 政次

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.48, no.9, pp.824-833, 1990

被引用文献数

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

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.47, no.7, pp.606-618, 1989

被引用文献数

1 19

---

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

常石 敬一

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.53, no.10, pp.922-923, 1995 (Released:2009-11-16)

著者

石川 延男 北爪 智哉

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.41, no.5, pp.432-438, 1983-05-01 (Released:2009-11-13)

参考文献数

24

被引用文献数

4 6

---

A number of “Grignard-type” reactions of organic fluorine compounds were achieved by treating perfluoroalkyl iodides and substrates with zinc under the irradiation of ultrasound. The reactions include 1) Direct carboxylation of perfluoroalkyl iodides, 2) Perfluoroalkylation of carbonyl compounds, 3) Perfluoroalkylation of allyl, vinyl and aryl halides, and 4) Hydroperfluoroalkylation of alkynes and dienes.

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.