Palladium(II) Acetate as Catalyst in Transvinylation Reactions of Hydroxycinnamic Acid and Its Derivatives

Kadidae, La Ode; Usami, Akira; Honda, M.

doi:10.14233/ajchem.2018.21033

Cited by 5 publications

(7 citation statements)

References 7 publications

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“…La(NO 3 ) 3 •H 2 O/ P(n-octyl) 3 was used as a catalyst for the transesterification reaction. 186 This report successfully obtained 1-CQA (1), 3-CQA (2), and 4-CQA (6) (Schemes 3 and 4) but failed to synthesize 5-CQA (9) (Scheme 4). 187 1-O-Methylchlorogenic acid (5-O-caffeoyl-1-methylquinic acid) (14) was first isolated from the aqueous ethanol extract of Phyllostachys edulis (Gramineae) leaves.…”

Section: Synthetic Approaches To Cqasmentioning

confidence: 84%

“…The hydroxyl groups of caffeic acid were protected with TBS, and the carboxyl group was esterified with vinyl. La(NO 3 ) 3 ·H 2 O/P( n -octyl) 3 was used as a catalyst for the transesterification reaction . This report successfully obtained 1-CQA ( 1 ), 3-CQA ( 2 ), and 4-CQA ( 6 ) (Schemes and ) but failed to synthesize 5-CQA ( 9 ) (Scheme ).…”

Section: Synthetic Approaches To Cqasmentioning

confidence: 99%

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Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis

Liu

Zhang

et al. 2020

J. Agric. Food Chem.

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Caffeoylquinic acids (CQAs) are a broad class of secondary metabolites that have been found in edible and medicinal plants from various families. It has been 100 years since the discovery of chlorogenic acid in 1920. In recent years, a number of naturally derived CQAs have been isolated and structurally elucidated. Accumulated evidence demonstrate that CQAs have a wide range of biological activities, such as antioxidation, antibacterial, antiparasitic, neuroprotective, anti-inflammatory, anticancer, antiviral, and antidiabetic effects. Up to date, some meaningful progresses on the biosynthesis and total synthesis of CQAs have also been made. Therefore, it is necessary to comprehensively summarize the structure, biological activity, biosynthesis, and chemical synthesis of CQAs. This review provides extensive coverage of naturally occurring CQAs discovered from 1990 until 2020. Modern isolation techniques, chemical data (including structure, biosynthesis, and total synthesis), and bioactivity are summarized. This would be helpful for further research of CQAs as potential pharmaceutical agents.

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Section: Synthetic Approaches To Cqasmentioning

confidence: 84%

Section: Synthetic Approaches To Cqasmentioning

confidence: 99%

Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis

Liu

Zhang

et al. 2020

J. Agric. Food Chem.

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“…Also, as can be seen, several of the assignments correspond to minor modifications of the structures described: Ethyl rosmarinate ( m/z 387.1080) 30 , Methyl rosmarinate ( m/z 373.0924) 30 , ethyl caffeate (m/z 207.0657) 30 , vinyl caffeate ( m/z 205.0501), carnosol, rosmanol and carnosic acid derivatives and acetylhorminone. Vinyl caffeate is not a rarity, it has been isolated from plants of the Perilla and Isodon genus ( Lamiaceae ) 42 , 43 , has described methods to synthesize it 44 , 45 and serves as a precursor to synthesize chlorogenic acids 46 . Also, note the presence of quinic acid ( m/z 191.0556) but with the absence of chlorogenic acids.…”

Section: Resultsmentioning

confidence: 99%

Phytochemical profile and rosmarinic acid purification from two Peruvian Lepechinia Willd. species (Salviinae, Mentheae, Lamiaceae)

Serrano

Villena

Rodríguez

2021

Sci Rep

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The phytochemical profile of Lepechinia meyenii (Walp.) Epling and Lepechina floribunda (Benth.) Epling obtained by liquid chromatography associated with high-resolution mass spectrometry is presented. Forty eight compounds were detected exhibiting a variety of salvianolic acids and abietane phenolic diterpenoids. A simple procedure by cold evaporative crystallization to purify rosmarinic acid from these botanical species was also shown.

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“…In a first set of experiments, ethyl 4-nitrobenzoate was investigated as acyl donor for N-and Oacylation, but no trace of reaction was observed. Since vinyl esters are more efficient acyl donors [16,17], activated vinyl 4-nitrobenzoate 4 was prepared exploiting a Pd(II)-catalysed transvinylation reaction starting from 4-nitrobenzoic acid [25]. First, the solubility of vinyl 4-nitrobenzoate 4 was evaluated in phosphate buffer (100 mM, pH = 8) in the presence of DMSO as a co-solvent (10% v/v) [16].…”

Section: Resultsmentioning

confidence: 99%

Efficient Chemo-Enzymatic Flow Synthesis of High Value Amides and Esters

et al. 2020

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A flow-based chemo-enzymatic synthesis of selected APIs (i.e., butacaine, procaine and procainamide) has been developed. A bioreactor made of MsAcT, a versatile acyltransferase from Mycobacterium smegmatis, immobilised on glyoxyl–garose, was exploited to efficiently prepare amide and ester intermediates in gram scale. Immobilised MsAcT was employed in pure organic solvent, demonstrating high stability and reusability. In-line purification of the key intermediates using polymer-bound sulphonyl chloride was added after the bioreactor, enhancing the automation of the process. A final hydrogenation step using the H-Cube reactor was further carried out to obtain the selected APIs in excellent yields (>99%), making the process fast, safe and easily handled.

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Palladium(II) Acetate as Catalyst in Transvinylation Reactions of Hydroxycinnamic Acid and Its Derivatives

Cited by 5 publications

References 7 publications

Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis

Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis

Phytochemical profile and rosmarinic acid purification from two Peruvian Lepechinia Willd. species (Salviinae, Mentheae, Lamiaceae)

Efficient Chemo-Enzymatic Flow Synthesis of High Value Amides and Esters

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