Isobenzofurans and ortho-benzoquinone monoketals in syntheses of xestoquinone and its 9- and 10-methoxy derivatives

Sutherland, Hamish S.; Higgs, Kerianne; Taylor, Nicholas J.; Rodrigo, R.

doi:10.1016/s0040-4020(00)00938-8

Cited by 49 publications

(27 citation statements)

References 22 publications

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“…Isolated Yield = 68% Scheme 1. amine (3). The voltammogram exhibits two cathodic peaks C 1 and C 0 (À0.12 V vs. SCE).…”

Section: Voltammetric Studiesmentioning

confidence: 99%

“…A vast number of quinones with great structural diversity are provided by nature; some of them play a major role in the redox electron-transport chains of living systems [1][2][3][4]. In addition, many drugs, such as doxorubicin, daunorubicin and mitomycin C in cancer chemotherapy contain quinones [5], whereas various other quinones have found uses in industry [6,7].…”

Section: Introductionmentioning

confidence: 99%

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Electrochemical synthesis of amino-substituted 1,2-benzoquinone derivatives

Nematollahi

Hesari

2005

Journal of Electroanalytical Chemistry

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“…Isolated Yield = 68% Scheme 1. amine (3). The voltammogram exhibits two cathodic peaks C 1 and C 0 (À0.12 V vs. SCE).…”

Section: Voltammetric Studiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Electrochemical synthesis of amino-substituted 1,2-benzoquinone derivatives

Nematollahi

Hesari

2005

Journal of Electroanalytical Chemistry

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“…A vast number of quinones with great structural divergence are provided by nature and play a major role in the redox electron-transport chains of living system [1][2][3]; for example, vitamin K is known in blood coagulation mechanism and photosynthesis, and ubiquinone and vitamin E are important factors in electron transport and oxidative phosphorylation. More complex quinonoic compounds are used extensively in medicine, especially as anticancer agents, and their activity stems from their special ability to undergo one-electron transfer reaction to form reactive radicals [4,5].…”

Section: Introductionmentioning

confidence: 99%

Electrochemical oxidation of catechol in the presence of an aromatic amine in aqueous media

et al. 2009

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The electrochemical oxidation of catechol has been studied in the presence of p-nitroaniline as a nucleophile in aqueous media at the surface of glassy carbon electrode, using cyclic voltammetry. The products of electrosynthesis have been purified and characterized by Fourier-transform infrared (FT-IR), 1 H nuclear magnetic resonance (NMR), 13 C NMR, and distortionless enhancement by polarization transfer (DEPT), and the mechanism of anodic oxidation was deduced from voltammetric and spectroscopic data.

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“…The latter could be converted to the target 108 by a Cope rearrangement. A similar approach was used in their synthesis of (G)-xestoquinone and derivatives [146,147].…”

Section: Diels-alder Cycloadditionsmentioning

confidence: 99%

Oxidative Conversion of Arenols into ortho ‐Quinols and ortho ‐Quinone Monoketals – A Useful Tactic in Organic Synthesis

Quideau

2002

Modern Arene Chemistry

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The oxidative activation of arenes is a powerful and versatile synthetic tactic that enables dearomatization to give useful synthons. Central to this chemistry are hydroxylated arenes or arenols, the phenolic functions of which can be exploited to facilitate the dearomatizing process by two-electron oxidation. Suitably substituted arenols can hence be converted, with the help of oxygen-or carbon-based nucleophiles, into ortho-quinone monoketals and ortho-quinols. These 6-oxocyclohexa-2,4-dienones are ideally functionalized for the construction of many complex and polyoxygenated natural product architectures. Today, the inherent and multiple reactivity of arenol-derived ortho-quinone monoketals and orthoquinols species is finding numerous and, in many cases, biomimetic applications in modern organic synthesis. 15.1

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Isobenzofurans and ortho-benzoquinone monoketals in syntheses of xestoquinone and its 9- and 10-methoxy derivatives

Cited by 49 publications

References 22 publications

Electrochemical synthesis of amino-substituted 1,2-benzoquinone derivatives

Electrochemical synthesis of amino-substituted 1,2-benzoquinone derivatives

Electrochemical oxidation of catechol in the presence of an aromatic amine in aqueous media

Oxidative Conversion of Arenols into ortho ‐Quinols and ortho ‐Quinone Monoketals – A Useful Tactic in Organic Synthesis

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