A Facile Approach to Synthesis of the Di‐<i>O</i>‐methyl Ethers of (−)‐Agatharesinol, (−)‐Sugiresinol, (+)‐Nyasol and (+)‐Tetrahydronyasol

Quan, Weiguo; Yu, Binxun; Zhang, Jiyong; Liang, Qiren; Sun, Yunjun; She, Xuegong; Pan, Xinfu

doi:10.1002/cjoc.200790129

Cited by 9 publications

(3 citation statements)

References 24 publications

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“…The fractions eluted with EtOH/H 2 O (95 : 5, v/v) and acetone/H 2 O (2 : 8, v/v) were separated by HPLC (Agilent 1100 HPLC, column: Zorbax 300SB-C18 PrepHT, 21.2 × 250 mm, 7 μ m; mobile phase: MeOH : H 2 O = 65 : 35; flow rate: 8 mL/min) to give 5 (107 mg), 6 (16 mg), 7 (18 mg), 8 (89 mg), 9 (18 mg), and 10 (47 mg). All the compounds were identified by NMR and MS spectroscopy and by comparison with spectral literature data [ 16 – 22 ].…”

Section: Methodsmentioning

confidence: 99%

Antioxidant Capacity and Proanthocyanidin Composition of the Bark of Metasequoia glyptostroboides

Chen

Zhang

Zong

et al. 2014

Evidence-Based Complementary and Alternative Medicine

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Metasequoia glyptostroboides Hu et Cheng is the only living species in the genus Metasequoia Miki ex Hu et Cheng (Taxodiaceae), which is well known as a “living fossil” species. In the Chinese folk medicine, the leaves and bark of M. glyptostroboides are used as antimicrobic, analgesic, and anti-inflammatory drug for dermatic diseases. This study is the first to report the free radical scavenging capacity, antioxidant activity, and proanthocyanidin composition of the bark of M. glyptostroboides. We observed total of six extracts and fractions, which were easily obtained by water-ethanol extraction and followed by a further separation with D101 resin column chromatography, had significant DPPH radical, superoxide anion radical, and hydroxyl radical scavenging capacity, total antioxidative capacity (T-AOC), lipid peroxidation inhibitory activity, and metal ions chelating capacity. The fraction MGEB, which was obtained by 60% ethanol extraction and followed by a further separation with D101 resin column chromatograph, possessed the highest proanthocyanidin content and the highest free radical scavenging and antioxidant activities. Furthermore, MGEB could significantly protect against CCl4 induced acute liver injury through inhibition of oxidative stress in mice. In addition, ten proanthocyanidins were isolated from MGEB, and six of them were firstly reported from this plant.

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Section: Methodsmentioning

confidence: 99%

Antioxidant Capacity and Proanthocyanidin Composition of the Bark of Metasequoia glyptostroboides

Chen

Zhang

Zong

et al. 2014

Evidence-Based Complementary and Alternative Medicine

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“…Wittig olefination gave diene 23 in 95% yield. 12 However, deprotection of 23 gave 24 in only moderate yield. Alcohol 24 is labile and decomposed slowly after isolation.…”

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confidence: 99%

First synthesis of an ABCE ring substructure of daphnicyclidin A

Clark

Harmata

2022

Org. Biomol. Chem.

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“…1,3-Biarylated carbonyl compounds are among the versatile intermediates in organic synthesis for the preparation of various biologically, naturally occurring compounds . Owing to their biological properties present in several small natural products and pharmaceutical agents (Figure ), many methods have been developed for their synthesis. − Carbonyl compounds with aldehyde functional groups are prone to undergo skeletal rearrangement to ketones via 1,2-group shift, and strategies used for the synthesis of diarylated ketone derivatives include C–H insertion of diazoalkane, Dakin–West syntheses, and the carbonylative coupling of benzyl bromide . However, for the direct construction of a C–C bond for preparing substituted carbonyl compounds, α-alkylation is one of the fundamental approaches in organic synthesis .…”

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confidence: 99%

Direct α-Benzylation of Methyl Enol Ethers with Activated Benzyl Alcohols: Its Rearrangement and Access to (±)-Tetrahydronyasol, Propterol A, and 1,3-Diarylpropane

Jena

Khan

2019

J. Org. Chem.

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Herein, we report a one-pot Lewis acid mediated synthesis of bi-and triarylpropanal derivatives and their corresponding isomeric ketones from aromatic enol ethers. This transformation takes place via nucleophilic attack of enol ethers to electron-rich benzyl alcohols. The substrate scope of this indicates that it might proceed via quinomethoxy methide as a key intermediate leading to propanal derivatives, and their Wagner−Meerwein rearrangement afforded isomeric ketones. Further, this methodology was applied for the synthesis of (±)-tetrahydronyasol, propterol A, and 1,3diarylpropane.

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A Facile Approach to Synthesis of the Di‐O‐methyl Ethers of (−)‐Agatharesinol, (−)‐Sugiresinol, (+)‐Nyasol and (+)‐Tetrahydronyasol

Cited by 9 publications

References 24 publications

Antioxidant Capacity and Proanthocyanidin Composition of the Bark of Metasequoia glyptostroboides

Antioxidant Capacity and Proanthocyanidin Composition of the Bark of Metasequoia glyptostroboides

First synthesis of an ABCE ring substructure of daphnicyclidin A

Direct α-Benzylation of Methyl Enol Ethers with Activated Benzyl Alcohols: Its Rearrangement and Access to (±)-Tetrahydronyasol, Propterol A, and 1,3-Diarylpropane

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