A re-investigation of resveratrol synthesis by Perkins reaction. Application to the synthesis of aryl cinnamic acids

Solladié, Guy; Pasturel‐Jacope, Yacine; Maignan, Jean

doi:10.1016/s0040-4020(03)00405-8

Cited by 86 publications

(52 citation statements)

References 8 publications

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“…1 H and 13 C{ 1 H} NMR spectra were referenced to residual protio impurities in the solvent ( 1 H) or the 13 General Procedure for Preparation of Aldehydes. 30 p-Hydroxybenzaldehyde (1 equiv) and K 2 CO 3 (3.2 equiv) were added as solids to 100 mL of Ar-purged DMF (ca. 100 mL) at room temperature.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Cobaltoporphyrin-Catalyzed CO₂/Epoxide Copolymerization: Selectivity Control by Molecular Design

et al. 2012

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A series of cobalt(III) chloride porphyrin complexes of the general formula 5,10,15,20-tetra(p-alkoxy)-phenylporphyrin cobalt chloride (4b−e) and the related 5,10,15,20-tetra(p-nitro)phenylporphyrin cobalt chloride (4f) are presented and their reactivity toward propylene oxide (PO)/CO 2 coupling/copolymerization is explored. While the nitro-substituted complex (4f), in conjunction with an onium salt, shows moderate activity toward cyclization, the 4b−e/ onium systems show superior copolymerization activity in comparison to tetraphenylporphyrin Co(III) chloride (4a) with high selectivity and conversion to poly(propylene carbonate) (PPC). A comprehensive copolymerization behavior study of the alkoxy-substituted porphyrin complexes 4b−e in terms of reaction temperature and CO 2 pressure is presented. Complexes bearing longer alkoxy-substituents demonstrate the highest polymerization activity and molecular weights, however all substituted catalyst systems display a reduced tolerance to increased temperature with respect to PPC formation. Studies of the resulting polymer microstructures show excellent head-totail epoxide incorporation and near perfectly alternating poly(carbonate) character at lower polymerization temperatures.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Cobaltoporphyrin-Catalyzed CO₂/Epoxide Copolymerization: Selectivity Control by Molecular Design

et al. 2012

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“…One such approach is the Perkin condensation, which is an efficient method for preparation of a-phenylcinnamic acids comprising the carbon framework of stilbenes [9].…”

Section: Introductionmentioning

confidence: 99%

Configuration of stilbene derivatives by 1H NMR and theoretical calculation of chemical shifts

Rotta

Neto

Lima

et al. 2010

Journal of Molecular Structure

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“…At present, many synthetic approaches for resveratrol and analogues have been designed through Wittig, 35,36) Horner, 37) Emmons-Wadsworth, 38) and Heck 39) reactions. Other methodologies involve lithiation-condensation, 40) Perkin, 41) Ramberg-Bäcklund, 42) or Diels-Alder/Wittig 43) reactions. The formation of carbon-carbon double bond in trans-configuration is the key step in the synthetic process.…”

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confidence: 99%

Efficient Synthesis of Natural Polyphenolic Stilbenes: Resveratrol, Piceatannol and Oxyresveratrol

Sun

Chen

Cai³

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Natural trans polyphenolic stilbenes were known to have numerous remarkable biological properties including beneficial effects on patients with cancers, cardiovascular diseases, viral infections, diabetes, dementia, and central nervous system (CNS) disorders. Among them, resveratrol, piceatannol and oxyresveratrol are recognized to be the representatives of trans-polyphenolic stilbenes (Fig. 1).Resveratrol (trans-3,4Ј,5-trimethoxystilbene) is a phytoalexin isolated from more than 70 plant species such as grapes, peanuts, and berries.1) It is now commercially produced from the roots of Polygonum cuspidatum, a plant used in traditional Chinese medicine for centuries. The biological activity of resveratrol has been well documented in recent years through a number of physiological and pharmacological studies which indicate that resveratrol plays an important role in prevention of cancers, 2-5) heart diseases, 6) neurodegenerative diseases 7) and inflammations. 8) Moreover, the radical scavenging, 9) antiviral, 10) antioxidant, 11) lipid modification 12) as well as platelet aggregation inhibition activities 13) associated with resveratrol have also been reported. Recently, resveratrol has been shown to extend lifespan of yeasts, Caenorhabditis elegans and Drosophila melanogaster through activation of sirtuins (SIRT-1, 2), a nicotinamide adenine dinucleotide (NAD) dependent histone deacetylase that has been shown to directly correlate with cellular longevity, 14) and to improve health and survival of mice on a high-calorie diet. 15)Piceatannol (trans-3,3Ј,4Ј,5-tetramethoxystilbene) is a tetrahydroxystilbene and a close analog of resveratrol with an additional aromatic hydroxyl group. It has been isolated from grapes together with resveratrol and several other traditional Chinese herbs. 16,17) Studies showed that piceatannol inhibits several tyrosine kinases involved in cell proliferation. 18-21)The anti-tyrosinase activity of piceatannol (IC 50 ϭ1.53 mM) was significantly higher than that of resveratrol (IC 50 ϭ 63.2 mM). In addition, recent studies indicated that the cancer preventative agent resveratrol is converted to anticancer agent piceatannol by cytochrome P450 enzyme CYP1B1 22) and piceatannol protects PC12 cells from hydrogen-peroxideand peroxynitrite-induced apoptosis by blocking the activation of c-Jun N-terminal kinase (JNK) and the down-regulation of Bcl-XL. 23)Oxyresveratrol (trans-2Ј,3,4Ј,5-tetramethoxystilbene), available from Morus alba Linne Artocarpus lakoocha Roxb and mulberry wood, is another hydroxylated analog of resveratrol with high similarity. It has been known that oxyresveratrol is transported to tissues at high rates resulting in a bioavailability of about 50%.24) Pharmacological studies have demonstrated that oxyresveratrol can be used as an active ingredient in dermatology, 25,26) and exhibiting potent inhibitory effects on cyclooxygenase, 27,28) rat liver mitochondrial ATPase activity 29) and dihydroxyphenylalanine (DOPA) oxidase activity.27) It has also been revealed that oxyresveratro...

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A re-investigation of resveratrol synthesis by Perkins reaction. Application to the synthesis of aryl cinnamic acids

Cited by 86 publications

References 8 publications

Cobaltoporphyrin-Catalyzed CO₂/Epoxide Copolymerization: Selectivity Control by Molecular Design

Cobaltoporphyrin-Catalyzed CO₂/Epoxide Copolymerization: Selectivity Control by Molecular Design

Configuration of stilbene derivatives by 1H NMR and theoretical calculation of chemical shifts

Efficient Synthesis of Natural Polyphenolic Stilbenes: Resveratrol, Piceatannol and Oxyresveratrol

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A re-investigation of resveratrol synthesis by Perkins reaction. Application to the synthesis of aryl cinnamic acids

Cited by 86 publications

References 8 publications

Cobaltoporphyrin-Catalyzed CO2/Epoxide Copolymerization: Selectivity Control by Molecular Design

Cobaltoporphyrin-Catalyzed CO2/Epoxide Copolymerization: Selectivity Control by Molecular Design

Configuration of stilbene derivatives by 1H NMR and theoretical calculation of chemical shifts

Efficient Synthesis of Natural Polyphenolic Stilbenes: Resveratrol, Piceatannol and Oxyresveratrol

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Cobaltoporphyrin-Catalyzed CO₂/Epoxide Copolymerization: Selectivity Control by Molecular Design

Cobaltoporphyrin-Catalyzed CO₂/Epoxide Copolymerization: Selectivity Control by Molecular Design