Metallic chalcogenolates mediated modular Michael-aldol cascade reaction: an easy route to multi-functionalized chalcogenides and Morita–Baylis–Hillman adducts

Sousa, Bruno A.; Keppler, Arthur F.; Gariani, Rogério A.; Comasseto, J. V.; Santos, Alcindo A. Dos

doi:10.1016/j.tet.2012.09.027

Cited by 11 publications

(6 citation statements)

References 23 publications

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“…Besides the nucleophilic characteristics of α‐AL, Sousa et al. have developed an interesting approach in which the use of β‐AL as a Michael acceptor in a cascade Michael–aldol reaction is described (Scheme ) . In this work, the reactions with aldehydes are performed in the presence of magnesium selenolate, which is generated in situ in the presence of a Grignard reagent.…”

Section: Synthetic Applications Of Angelica Lactonesmentioning

confidence: 99%

“…Besides the nucleophilicc haracteristics of a-AL, Sousa et al have developed an interesting approachi nw hich the use of b-AL as aM ichael acceptor in ac ascade Michael-aldol reaction is described( Scheme 42). [72] In this work, the reactions with aldehydes are performed in the presence of magnesium selenolate, which is generatedi nsitu in the presence of aG rignard reagent. Concerning the mechanism of the reaction, 1,4-nucleophilic addition of the organometallic nucleophile to the bute-nolide takes place first to afford the enolatei ntermediate, which undergoes the aldol reaction with aldehydes 53.A lthought he reactivityo fb-AL is lower than that of other electrophilics pecies employed in this protocol, the reactions with aromatic and aliphatic aldehydes proceed well and afford products 54 in good to moderate yields (Scheme 42 b).…”

Section: B-angelica Lactone As Michael Acceptors In Ac Ascade Michaelmentioning

confidence: 99%

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Angelica Lactones: From Biomass‐Derived Platform Chemicals to Value‐Added Products

et al. 2017

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The upgrading of biomass‐derived compounds has arisen in recent years as a very promising research field in both academia and industry. In this sense, a lot of new processes and products have been developed, often involving levulinic acid as a starting material or intermediate. In the last few years, though, other scaffolds have been receiving growing attention, especially, angelica lactones. Considering these facts and the emergent applications of said molecules, in this review we will discuss their preparation and applications; the use of these frameworks as starting materials in organic synthesis to produce potential bioactive compounds will be covered, as will their use as a foundation to highly regarded compounds such as liquid alkanes with prospective use as fuels and polymers.

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Section: Synthetic Applications Of Angelica Lactonesmentioning

confidence: 99%

Section: B-angelica Lactone As Michael Acceptors In Ac Ascade Michaelmentioning

confidence: 99%

Angelica Lactones: From Biomass‐Derived Platform Chemicals to Value‐Added Products

et al. 2017

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“…The organotelluride compounds (Fig. 1) were synthesized as previously described (38)(39)(40)(41). All compounds were stored in a desiccator at 4°C, and stock solutions were prepared in DMSO.…”

Section: Methodsmentioning

confidence: 99%

Synthetic Organotellurium Compounds Sensitize Drug-Resistant Candida albicans Clinical Isolates to Fluconazole

Sá

Toledo

Gonçalves

et al. 2017

Antimicrob Agents Chemother

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Invasive Candida albicans infections are a serious health threat for immunocompromised individuals. Fluconazole is most commonly used to treat these infections, but resistance due to the overexpression of multidrug efflux pumps is of grave concern. This study evaluated the ability of five synthetic organotellurium compounds to reverse the fluconazole resistance of C. albicans clinical isolates. Compounds 1 to 4, at Ͻ10 g/ml, ameliorated the fluconazole resistance of Saccharomyces cerevisiae strains overexpressing the major C. albicans multidrug efflux pumps Cdr1p and Mdr1p, whereas compound 5 only sensitized Mdr1p-overexpressing strains to fluconazole. Compounds 1 to 4 also inhibited efflux of the fluorescent substrate rhodamine 6G and the ATPase activity of Cdr1p, whereas all five of compounds 1 to 5 inhibited Nile red efflux by Mdr1p. Interestingly, all five compounds demonstrated synergy with fluconazole against efflux pump-overexpressing fluconazoleresistant C. albicans clinical isolates, isolate 95-142 overexpressing CDR1 and CDR2, isolate 96-25 overexpressing MDR1 and ERG11, and isolate 12-99 overexpressing CDR1, CDR2, MDR1, and ERG11. Overall, organotellurium compounds 1 and 2 were the most promising fluconazole chemosensitizers of fluconazole-resistant C. albicans isolates. Our data suggest that these novel organotellurium compounds inhibit pump efflux by two very important and distinct families of fungal multidrug efflux pumps: the ATP-binding cassette transporter Cdr1p and the major facilitator superfamily transporter Mdr1p.

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“…In 2012, dos Santos et al described that polyfunctionalized γ-hydroxychalcogenides could be easily obtained from cascade Michael/aldol reactions promoted by chalcogenolates (Scheme ). , …”

Section: Lewis Base Catalysismentioning

confidence: 99%

Recent Advances in Catalytic Systems for the Mechanistically Complex Morita–Baylis–Hillman Reaction

et al. 2023

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Since its discovery in the late 1960s, the Morita–Baylis–Hillman (MBH) reaction has remained a powerful carbon–carbon σ-bond-forming transformation, producing small polyfunctionalized molecules. While commonly catalyzed by Lewis basic organic molecules such as tertiary amines and phosphines, several advances in functional catalysts and reaction conditions have been made in order to improve the reaction rate, substrate scope, and enantioselectivity. The goal of this Review is to give an updated summary of the main improvements made in catalytic systems for the MBH reaction over the past decade until nowadays. We hope this account will instigate further investigations in order to circumvent the remaining challenges of this fascinating transformation.

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Metallic chalcogenolates mediated modular Michael-aldol cascade reaction: an easy route to multi-functionalized chalcogenides and Morita–Baylis–Hillman adducts

Cited by 11 publications

References 23 publications

Angelica Lactones: From Biomass‐Derived Platform Chemicals to Value‐Added Products

Angelica Lactones: From Biomass‐Derived Platform Chemicals to Value‐Added Products

Synthetic Organotellurium Compounds Sensitize Drug-Resistant Candida albicans Clinical Isolates to Fluconazole

Recent Advances in Catalytic Systems for the Mechanistically Complex Morita–Baylis–Hillman Reaction

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