Stereoselective Synthesis of (E)‐Hydroxystilbenoids by Ruthenium‐Catalyzed Cross‐Metathesis.

Ferré-Filmon, Karine; Delaude, Lionel; Demonceau, Albert; Noels, Alfred F.

doi:10.1002/chin.200547092

Cited by 5 publications

(7 citation statements)

References 42 publications

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“…The synthesis of resveratrol can be achieved using Wittig or Wittig-Horner reactions with ruthenium-catalyzed cross-metathesis ( Fig. (4)) [29]. Further, potent analogues of resveratrol can be synthesized to test for enhanced biological activities.…”

Section: Resveratrol Chemistry -Natural Sources Synthesis and Analoguesmentioning

confidence: 99%

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The Cardiovascular Nutrapharmacology of Resveratrol: Pharmacokinetics, Molecular Mechanisms and Therapeutic Potential

Kroon¹,

Iyer²,

Chunduri³

et al. 2010

CMC

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Red wine contains many compounds that may have therapeutic use, including resveratrol (3,4',5-trihydroxytrans-stilbene). Since resveratrol could be administered both in the diet and as a therapeutic agent, defining appropriate concentrations requires understanding of the pharmacokinetics. Resveratrol absorption is rapid but plasma concentrations are low as it is rapidly and efficiently converted into relatively hydrophilic phase-2 conjugates, and metabolites, which are then rapidly excreted via the urine and bile. Resveratrol is an effective antioxidant in vivo by increasing NO synthesis and also maintaining the reduced intracellular redox state via the thioredoxin system. Further, activation of sirtuins (one class of lysine deacetylases) may mediate the cardiovascular responses shown by resveratrol. Studies on animal models of human disease suggest that resveratrol has the potential to decrease cardiovascular symptoms in patients with myocardial infarction, arrhythmias, hypertension, cardiomyopathies, fibrosis, atherosclerosis, thrombosis and diabetes, but, as yet, human clinical trials are rare. Cardioprotection by resveratrol in rodent models may rely on mechanisms producing pharmacological preconditioning in the heart including reducing reactive oxygen species, improving vasorelaxation and angiogenesis, preventing inflammation and apoptosis, delaying atherosclerosis as well as decreasing cardiovascular remodelling. Interventional studies in humans need to be completed before resveratrol can be considered as a standard therapeutic agent. Therefore, future studies should focus on obtaining the level of evidence required to determine whether resveratrol can be added to the list of evidence-based therapies for cardiovascular diseases that includes renin-angiotensin system inhibitors, beta-adrenoceptor antagonists and calcium entry blockers.

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Section: Resveratrol Chemistry -Natural Sources Synthesis and Analoguesmentioning

confidence: 99%

“…(4). Synthesis of resveratrol by Wittig or Wittig-Horner reactions using ruthenium-catalyzed cross-metathesis [29]. gates during the first pass and metabolites are rapidly excreted via the urine and bile.…”

Section: Distribution and Tissue Accumulationmentioning

confidence: 99%

The Cardiovascular Nutrapharmacology of Resveratrol: Pharmacokinetics, Molecular Mechanisms and Therapeutic Potential

Kroon¹,

Iyer²,

Chunduri³

et al. 2010

CMC

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“…Heterocoupling is only possible when one of the substrates is introduced in excess. Ali et al (1992) [34] synthesised symmetrical stilbene derivatives (37) by aryl aldehydes (36) reductive coupling in THF containing TiCl 4 and Zn as reducing agent (Scheme 2.16).…”

Section: Mcmurry Couplingmentioning

confidence: 99%

“…Indeed, this cross-metathesis can also provide an easy access to stilbenoid derivatives. Ferré-Filmon et al in 2005 [36] reported the construction of symmetrical and unsymmetrical (E)-polymethoxystilbene and (E)-polyhydroxystilbene derivatives by ruthenium-catalyzed crossmetathesis with help of second generation Grubbs catalysts (Scheme 2.17). They were of the opinion that the selectivity of the unsymmetrical cross-product can be enhanced almost up to 95% yield by introducing one of the reacting substrates in excess.…”

Section: Ruthenium-catalysed Cross-metathesismentioning

confidence: 99%

Strategies and Methods for the Syntheses of Natural Oligomeric Stilbenoids and Analogues

Velu

Thomas

Weber

2012

COC

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This review covers synthetic work carried out in the field of stilbene and oligostilbene chemistry. It includes a brief overview of the methods used for the synthesis of monomeric stilbenoids. The production of oligomeric species by means of enzymatic or microbial conversion is examined in detail. Biomimetic syntheses of stilbene oligomers are then scrutinised. Most of the work is based on the dimerisation of stilbenoid monomers with help of one-electron oxidants or through acid catalysis. Mechanistic interpretations of the oxidative couplings observed by the various groups are proposed and suggest that the outcome of these reaction be guided by the "hard and soft acid and base" (HSAB) principle together with supramolecular interactions between the reacting stilbenoid monomers. Eventually, the few non-biomimetic full syntheses are presented and their strategies analysed.

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“…Although stilbene itself is not a natural product, a large number of its derivatives have been isolated from various plant species [1]. Because of the wide range of biological activities and potential therapeutic value of the naturally occurring polyhydroxystilbenes, these compounds have received considerable attraction.…”

Section: Introdutionmentioning

confidence: 99%

Palladium Catalyzed Decarbonylative Mizoroki-Heck Reactions of Benzoyl Chloride and Styrene Under Microwave Irradiation

Martins¹,

Álvarez²,

Aguiar³

et al. 2007

LOC

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Stereoselective Synthesis of (E)‐Hydroxystilbenoids by Ruthenium‐Catalyzed Cross‐Metathesis.

Cited by 5 publications

References 42 publications

The Cardiovascular Nutrapharmacology of Resveratrol: Pharmacokinetics, Molecular Mechanisms and Therapeutic Potential

The Cardiovascular Nutrapharmacology of Resveratrol: Pharmacokinetics, Molecular Mechanisms and Therapeutic Potential

Strategies and Methods for the Syntheses of Natural Oligomeric Stilbenoids and Analogues

Palladium Catalyzed Decarbonylative Mizoroki-Heck Reactions of Benzoyl Chloride and Styrene Under Microwave Irradiation

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