374. Reduction products of the cyclopentadiene–benzoquinone adduct

Cookson, R. C.; Hill, R. R.

doi:10.1039/jr9630002023

Cited by 8 publications

(7 citation statements)

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“…3 In fact, Huisgen zwitterions are very often involved in many annulation reactions to construct heterocycles. Early reports about the annulations of Huisgen zwitterions can be traced back to 1960s when Cookson 57 first reported its cyclization with dimethyl acetylenedicarboxylate (DMAD) to form pyrazoles 120, and Huisgen 56 reported its annulations with isocyanates or isothiocyanates to produce triazole products 121 (Scheme 43).…”

Section: Based On Dialkyl Azodicarboxylates Substratesmentioning

confidence: 99%

Recent advances in stoichiometric phosphine-mediated organic synthetic reactions

2013

RSC Adv.

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Silong Xu a and Zhengjie He* b Organic synthetic reactions mediated by tertiary phosphines have attracted much attention in the organic chemistry community in the past two decades. These reactions can be divided into two categories: phosphine-catalyzed and stoichiometric phosphine-mediated transformations. While the phosphinecatalyzed reactions mechanistically rely on the unique properties of tertiary phosphines such as excellent nucleophilicity and good leaving group ability, the stoichiometric transformations are usually driven by nucleophilicity and strong oxyphilicity of tertiary phosphines. Since tertiary phosphines represent an important class of versatile chemical reagents in organic synthesis, stoichiometric phosphine-mediated reactions have recently demonstrated their uniqueness and high efficiency in organic synthesis, particularly with respect to the construction of carbon-carbon and carbon-heteroatom bonds, and therefore have stimulated much research interest. In this review, recent advances in stoichiometric phosphine-mediated reactions primarily including olefinations and annulations are summarized.

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Section: Based On Dialkyl Azodicarboxylates Substratesmentioning

confidence: 99%

Recent advances in stoichiometric phosphine-mediated organic synthetic reactions

2013

RSC Adv.

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“…Huisgen 内盐参与的环化反应最早可以追溯至 20 世纪 60 年代, Cookson 等 [13] 首次报道了 Ph 3 P 促进下 DEAD 1a 与丁炔二甲酸二甲酯(3)的环化反应, 以中等收率生成了吡唑衍生物 4a. 作者认为该反应起始于 Ph 3 P 与 1a 形成的鏻盐中间体 2a' (Scheme 2a).…”

Section: Huisgen 内盐的早期研究unclassified

Progress in Annulation Reactions Based on Huisgen Zwitterion

Liu¹,

Zhou²

2019

Chin. J. Org. Chem.

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The development of highly efficient and selective synthetic methodologies is an important research task in organic chemistry. In recent years, the Huisgen zwitterions, a type of intermediates derived from nucleophilic addition of tertiary phosphine to azodicarboxylates, have shown unique superiority and efficiency in synthesis of azacyclic compounds, and therefore have attracted broad interest from organic chemists. A large number of annulation reactions based on Huisgen zwitterions have been reported. According to the types of electrophiles, the annulation reactions of Husigen zwitterions with carbonyl compounds, electron-deficient alkenes, imines, and other electrophiles are summarized, respectively.

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“…Since this synthesis af the desired starting material appeared impractical an a large scale, we saught a more canvenient pracedure. The reactian af an a,a'-dibramaketane with furan in the presence af sadium iadide has given the expected bicyclic praduct (12), but in the case af 1,3-dibramo-3-methylbutan-2-ane, this technique was unpramising. In the presence af zinc and acetic acid, hawever, this dibramaketane and furan gave the desired adduct smaathly in ca.…”

Section: Xmentioning

confidence: 99%

An approach to the synthesis of pederin

Meinwald¹

1977

Pure and Applied Chemistry

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-Pederin, the vesicant component found in the haemolymph of many species of the staphylinid beetle of the genus Paederus, is a powerful inhibitor of protein synthesis in eucaryotic cells. Hith its nine chiral centers and its unusual functfonality, it is also the most complex, non-proteinaceous insect defensive compound known. This paper describes our progress toward a total synthesis of this fascinating natural product.Nature' s use of organic chemieals for .defensive purposes is one of the most intriguing areas of "applied organic chemistry". Arthropods are particularly skillful chemists (1); their defensive agents range from the elegant simplicity of single carbon compounds such as hydrogen cyanide and formic acid, through a variety of simple aliphatic compounds, to quinones, terpenes and "alkaloids" (2). Probably the most complex, non-proteinaceous defensive compound so far characterized is produced by staphylinid beetles of the genus Paederus (known in East Africa as the "Nairobi Eye Fly"). The dramatic vesicant properties of these be~tles were first described in 1912 (3), although the isolation of pederin (the haemolymph component responsible for the vesicant effect) in crystalline form and the demonstration that pederin is different from the notorious insect product cantharidin (another vesicant of considerable interest) are more recent (4).Extensive chemical and spectral studies were carried out on pederin in Italy (5) and in Japan (6), culminating in X-ray crystallographic studies (7) which resulted in tae determination of both its structure and absolute stereochemistry.

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374. Reduction products of the cyclopentadiene–benzoquinone adduct

Cited by 8 publications

References 0 publications

Recent advances in stoichiometric phosphine-mediated organic synthetic reactions

Recent advances in stoichiometric phosphine-mediated organic synthetic reactions

Progress in Annulation Reactions Based on Huisgen Zwitterion

An approach to the synthesis of pederin

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