Tellurium in organic synthesis: synthesis of bioactive butenolides

Bassora, Bruno K.; Costa, Carlos Eduardo da; Gariani, Rogério A.; Comasseto, J. V.; Santos, Alcindo A. Dos

doi:10.1016/j.tetlet.2006.12.063

Cited by 31 publications

(10 citation statements)

References 28 publications

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“…after column chromatography purification. 54 It was reported that this lactone acts in the glutathione S-transferase (GST) detoxification system when dietary administrated to Wistar rats. Racemic 21 and 22 were also obtained in 50 and 72% yield, respectively, by the same procedure from the corresponding tellurides.…”

Section: Application Of the Te / Metal Exchange Reaction In The Synthmentioning

confidence: 99%

“…Butenolide 21 have moderate activity against filamentous fungi and antifungal activity against human pathogens whereas 22 is a metabolite of Streptomyces griseus (Scheme 15). 54 This strategy was applied as a key step for the construction of the lactone ring in the total synthesis of (+)-blastmycinone (30), (-)-blastmycinolactol (28), (+)-antimycinone (31) and (-)-NFX-2 (29). 55 These compounds are degradation products of macrocyclic dilactone (+)-antimycin A (32) (Scheme 16) and exhibit a number of biological activities.…”

Section: Application Of the Te / Metal Exchange Reaction In The Synthmentioning

confidence: 99%

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Reactive organometallics from organotellurides: application in organic synthesis

Princival

Santos

Comasseto

2010

J. Braz. Chem. Soc.

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Neste artigo é revisada a preparação de organometálicos reativos a partir de teluretos orgânicos. É comentado o uso dos organometálicos preparados dessa maneira na síntese de substâncias bioativas.In this paper the preparation of reactive organometallics starting from organotellurides is reviewed. The application of the reactive organometallics prepared in this way in the synthesis of bioactive compounds is commented.

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Section: Application Of the Te / Metal Exchange Reaction In The Synthmentioning

confidence: 99%

Section: Application Of the Te / Metal Exchange Reaction In The Synthmentioning

confidence: 99%

Reactive organometallics from organotellurides: application in organic synthesis

Princival

Santos

Comasseto

2010

J. Braz. Chem. Soc.

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“…On the other hand, Pd 19,30 and Ni 24,[31][32][33] catalyzed cross coupling reactions and tellurium/metal exchange reactions [34][35][36][37][38][39][40][41][42] are demonstrative of the usefulness of vinylic tellurides.…”

Section: Introductionmentioning

confidence: 99%

Iron-catalyzed coupling reactions of vinylic chalcogenides with Grignard reagents

Silveira¹,

Mendes²,

Wolf³

2010

J. Braz. Chem. Soc.

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Este trabalho descreve um novo método para a reação de acoplamento entre selenetos e teluretos vinílicos e reagentes de Grignard, catalisada por Fe(acac) 3 e à temperatura ambiente. A reação ocorre com retenção da configuração, fornecendo os respectivos alquenos em bons a excelentes rendimentos. Este método também é eficiente para a reação de acoplamento de calcogenetos bisvinílicos com reagentes de Grignard.A general new method for the cross-coupling reaction between vinylic selenides and tellurides and Grignard reagents catalyzed by Fe(acac) 3 at room temperature is described. This reaction proceeded with retention of configuration, providing the respective alkenes in good to excellent yields. This method is also efficient for the coupling reaction of divinyl chalcogenides with Grignard reagents. Keywords: iron-catalyzed, vinylic chalcogenides, cross-coupling, Grignard reagents IntroductionOrganochalcogenium compounds became the key component of a variety of versatile and useful reagents for organic synthesis. The multiple applications of organochalcogenium chemistry have been well described in a number of review articles 1-6 and books. 7-11 Functionalized alkynyl 12-18 and alkenyl [19][20][21][22][23] chalcogenides have a great potential in organic synthesis, since they are valuable intermediates for the selective preparation of several organic compounds.Among the many applications of vinylic selenides, divinylic selenides and vinylic sulfides, the cross-coupling reaction with Grignard reagents catalyzed by Ni 18,24-27 and Pd 28,29 to give the corresponding cross-coupled products, has been described. On the other hand, Pd 19,30 and Ni 24,[31][32][33] catalyzed cross coupling reactions and tellurium/metal exchange reactions [34][35][36][37][38][39][40][41][42] are demonstrative of the usefulness of vinylic tellurides.Transition-metal-catalyzed C-C bond coupling reactions are very important in many areas of science. 43,44 Most current methods require expensive transitionmetal catalysts and ligands. However, in the last years Fe-catalyzed C-C bond cross coupling reactions of vinylic substrates and Grignard reagents became a subject of intense interest. [45][46][47][48][49][50][51] The vinylic counterpart is quite broad in scope, since vinylic halides, triflates, sulfonates, tosylates and enol phosphates can be used. [45][46][47][48][49][50][51] In continuation to our interest on the synthesis and synthetic applications of vinylic chalcogenides 52-58 we decided to study the feasibility of their use in cross coupling reaction with Grignard species catalyzed by iron. To the best of our knowledge, iron catalysts have never been used for the coupling of vinylic selenides and tellurides as electrophiles. The possible use of iron catalysts would represent a great improvement over the high cost of palladium precursors and from the concerns about the toxicity of nickel salts. In light of the above comments it is of interest to design a simple, efficient, and versatile method for the stereoselective coupling of vinylic se...

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“…Recently, our research group has been working in the preparation and application of hydroxy tellurides in the tellurium/lithium exchange reaction. These compounds have been efficiently used as alternative organometallic sources of 1,4-dianion intermediates in the synthesis of diols [8], spiroketals [9], bioactive butenolides [10], and in the synthesis of natural products, such as (±)-frontalin [11] and (+)-endo-brevicomin [12]. The interesting results obtained with oxygen-containing organotellurium compounds served as inspiration for the design and application of many other functionalized organotellurium compounds.…”

Section: Introductionmentioning

confidence: 99%

“…In this way, following our current interest in the development and application of functionalized organotellurium compounds in organic synthesis [8][9][10][11][12], we report herein the preparation of a modular series of nitrogen-containing organotellurium compounds and their selenium and sulfur analogues via the ring-opening reaction of easily available aziridines, as depicted in Fig. 1.…”

Section: Introductionmentioning

confidence: 99%

Practical synthesis of chiral β-telluro amines by ring-opening reaction of aziridines

Vargas

Comasseto

2009

Journal of Organometallic Chemistry

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Tellurium in organic synthesis: synthesis of bioactive butenolides

Cited by 31 publications

References 28 publications

Reactive organometallics from organotellurides: application in organic synthesis

Reactive organometallics from organotellurides: application in organic synthesis

Iron-catalyzed coupling reactions of vinylic chalcogenides with Grignard reagents

Practical synthesis of chiral β-telluro amines by ring-opening reaction of aziridines

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