Synthesis of thomasidioic acid

Ahmed, Riaz; Lehrer, Michael; Stevenson, Robert

doi:10.1016/s0040-4039(01)95701-6

Cited by 13 publications

(10 citation statements)

References 7 publications

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“…The identification was confirmed by comparison with an authentic sample of thomasidioic acid synthesized from sinapic acid. The NMR spectrum of the synthetic thomasidioic acid coincided with the spectrum found in the literature (19)(20)(21) and was identical to the thomasidioic acid produced from sinapic acid in basic buffer (Tables 1 and 2).…”

Section: Resultssupporting

confidence: 80%

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Conversion of phenolics to lignans: Sinapic acid to thomasidioic acid

Rubino

Arntfield

Charlton

1995

J Americ Oil Chem Soc

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Changes in sinapic acid when exposed to aqueous alkaline conditions were elucidated. Sinapic acid was exposed to a volatile buffer (pH 8.5) for 24 h, lyophilized, acidified, extracted, and characterized using nuclear magnetic resonance and mass spectroscopy. The product obtained was identified as the lignan thomasidioic acid. This identification was confirmed by comparison with a synthesized authentic sample of thomasidioic acid. Conversion of sinapic acid to thomasidioic acid under alkaline conditions previously has not been reported. Thomasidioic acid was present after exposure of sinapic acid to pH 8.5 for as few as 6 h. Thomasidioic acid also was formed at pH 7.JAOCS 72, 1465-I 470 (t 995).

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Section: Resultssupporting

confidence: 80%

“…Synthesis ofthomasidioic acid. Sinapic acid (40 mg) was converted to dehydrosinapic acid dilactone (Scheme 1) by treating with FeC13 in the presence of 02, using the method previously described (19,20). The lactone was converted to thomasidioic acid by a brief treatment (30 s) with concentrated H2SO4, followed by dilution with cold water.…”

Section: Methodsmentioning

confidence: 99%

Conversion of phenolics to lignans: Sinapic acid to thomasidioic acid

Rubino

Arntfield

Charlton

1995

J Americ Oil Chem Soc

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“…On the other hand POC of SinA mediated by FeCl 3 and O 2 , produced dilactone 1d in 73% yield (Scheme 8) [26]. Dilactone 1d , on treatment with aqueous acid, rearranges to ThoA ( 8 ), whereas with methanolic HCl, 1d is converted to its corresponding diester 9a [27,28]. The dimethyl ether 9b of the latter can be hydrogenated to produce a mixture of the diastereomeric aryltetralins 10a and 10b , of which the former was reduced to (±)-lyoniresinol dimethyl ether ( 11 ) [29,30].…”

Section: Lignan Skeleton Assembly With β-β Bond Formation As the Kmentioning

confidence: 99%

Bioinspired Syntheses of Dimeric Hydroxycinnamic Acids (Lignans) and Hybrids, Using Phenol Oxidative Coupling as Key Reaction, and Medicinal Significance Thereof

Magoulas

Papaioannou

2014

Molecules

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Lignans are mainly dimers of 4-hydroxycinnamic acids (HCAs) and reduced analogs thereof which are produced in Nature through phenol oxidative coupling (POC) as the primary C-C or C-O bond-forming reaction under the action of the enzymes peroxidases and laccases. They present a large structural variety and particularly interesting biological activities, therefore, significant efforts has been devoted to the development of efficient methodologies for the synthesis of lignans isolated from natural sources, analogs and hybrids with other biologically interesting small molecules. We summarize in the present review those methods which mimic Nature for the assembly of the most common lignan skeleta by using either enzymes or one-electron inorganic oxidants to effect POC of HCAs and derivatives, such as esters and amides, or cross-POC of pairs of HCAs or HCAs with 4-hydrocycinnamyl alcohols. We, furthermore, provide outlines of mechanistic schemes accounting for the formation of the coupled products and, where applicable, indicate their potential application in medicine.

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“…Several synthetic methods have been developed to prepare racemic trans thomasidioic acid: Stobbe condensation of 3,4,5-trimethoxybenzaldehyde with dimethylsuccinate [ 21 ]; alkaline treatment of sinapic acid 2 [ 22 ], oxidative coupling of sinapic acid 2 [ 23 ] or of sinapic acid methyl ester 3d [ 24 ] with ferric chloride in aqueous acetone ( Scheme 2 ). Higher yields were obtained using hydrogen peroxide as the oxidant and horseradish peroxidase as the catalyst [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Biomimetic Oxidations of Phenols: The Mechanism of the Diastereo- and Enantioselective Synthesis of Thomasidioic Acid

et al. 2008

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Enantiopure chiral amidic derivatives of sinapic acid were oxidised with hydrogen peroxide using horseradish peroxidase (HRP) as the catalyst to give the aryltetraline dilignol thomasidioic acid. Trans-diastereoselectivity and enantioselectivity in the formation of thomasidioic acid was observed. Computational methods show that the enantioselectivity is controlled by the β-β oxidative coupling step, while the diastereoselectivity is controlled by the stability of the reactive conformation of the intermediate quinomethide.

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Synthesis of thomasidioic acid

Cited by 13 publications

References 7 publications

Conversion of phenolics to lignans: Sinapic acid to thomasidioic acid

Conversion of phenolics to lignans: Sinapic acid to thomasidioic acid

Bioinspired Syntheses of Dimeric Hydroxycinnamic Acids (Lignans) and Hybrids, Using Phenol Oxidative Coupling as Key Reaction, and Medicinal Significance Thereof

Asymmetric Biomimetic Oxidations of Phenols: The Mechanism of the Diastereo- and Enantioselective Synthesis of Thomasidioic Acid

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