Intramolecular Diels−Alder and Cope Reactions of <i>o</i>-Quinonoid Monoketals and Their Adducts:  Efficient Syntheses of (±)-Xestoquinone and Heterocycles Related to Viridin

Carlini, Rina; Higgs, Kerianne; Older, Christina M.; Randhawa, Sab; Rodrigo, R.

doi:10.1021/jo970394l

Cited by 60 publications

(32 citation statements)

References 12 publications

(9 reference statements)

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“…The one-pot reaction of allylic alcohols with phenols to give bicyclo[2,2,2]octenones via an in situ intramolecular Diels Alder reaction has been described by Liao using diacetoxyiodobenzene (DAIB) as the oxidant [10], and by Rodrigo using bis-trifluoroacetoxyiodobenzene (BTFAIB) [11] (Scheme 1). Ortho-benzoquinones have also been generated electrochemically [12].…”

Section: Introduction Results and Discussionmentioning

confidence: 99%

“…In particular, the use of secondary and tertiary allylic alcohols was a significant extension of literature chemistry. It was found that BTFAIB [12,15], as exemplified by Rodrigo, was a more effective, higher yielding oxidant and this was used in preference to DAIB [11]. A series of substituted with substituted allylic alcohols.…”

Section: Introduction Results and Discussionmentioning

confidence: 99%

“…Template (11) was derived from the homologous acetic acid ester, whereas 13 and 14 have an ester link via the phenol ether, leading to a very different template topology. Unfortunately, it did not prove possible to make analogous templates of 13 and 14…”

Section: Introduction Results and Discussionmentioning

confidence: 99%

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Synthesis and agrochemical screening of a library of natural product-like bicyclo[2,2,2]octenones

Smith¹,

James²,

Abelman³

et al. 2005

CCHTS

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A general route to a series of differentially substituted bicyclo[2,2,2]octenones has been developed, making use of the in situ intramolecular Diels Alder reaction of masked ortho-benzoquinones. This approach was used to synthesize a series of thirteen key acid-containing templates from which a solution phase discovery library of 1126 diverse amides was then constructed. The rigid polycyclic nature of the templates and the prevalence of oxygenated functionality confer natural product-like qualities and three-dimensional diversity. The library was screened in HTS in vivo against a number of weed, insect and fungal model organisms leading to the discovery of a novel series of herbicidally active compounds. The development, production and biological activity of the library are described.

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Section: Introduction Results and Discussionmentioning

confidence: 99%

Section: Introduction Results and Discussionmentioning

confidence: 99%

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Synthesis and agrochemical screening of a library of natural product-like bicyclo[2,2,2]octenones

Smith¹,

James²,

Abelman³

et al. 2005

CCHTS

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“…The known 12 dienol 7 prepared from propargylic alcohol in four steps and 63% yield was subjected to our obenzoquinone monoketal, Diels-Alder protocol 8 with methylguaiacol 8 and [bis(trifluoroacetoxy)iodo]benzene to provide a mixture of adducts 9 and 10 which were not easily separated from each other. The mixture was therefore refluxed in 1,2,4-trimethylbenzene for 48 h to convert 10 to 9 by means of the Cope rearrangement.…”

Section: Resultsmentioning

confidence: 99%

A Short Synthesis of (±)-Halenaquinone

2001

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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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Intramolecular Diels−Alder and Cope Reactions of o-Quinonoid Monoketals and Their Adducts: Efficient Syntheses of (±)-Xestoquinone and Heterocycles Related to Viridin

Cited by 60 publications

References 12 publications

Synthesis and agrochemical screening of a library of natural product-like bicyclo[2,2,2]octenones

Synthesis and agrochemical screening of a library of natural product-like bicyclo[2,2,2]octenones

A Short Synthesis of (±)-Halenaquinone

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

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