A Mild Anionic Method for Generating <i>o-</i>Quinone Methides:  Facile Preparations of <i>Ortho</i>-Functionalized Phenols

Jones, Ryan M.; Water, Ryan W. Van De; Lindsey, Christopher C.; Hoarau, Christophe; Ung, and Thay; Pettus, Thomas R. R.

doi:10.1021/jo001752e

Cited by 47 publications

(25 citation statements)

References 10 publications

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“…4). Addition of BH 3 ·Me 2 S simply reduced the aldehyde and furnished alcohol 18 upon work-up [6]. If lithium was present in the solution, as shown with l -selectride, the carbonate underwent migration upon generation of the benzyl alkoxide to furnish phenol 19 .…”

Section: Resultsmentioning

confidence: 99%

New strategies for natural products containing chroman spiroketals

Green

Burnett

Pettus

2012

Pure and Applied Chemistry

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Two cycloaddition strategies are described that lead to various chroman spiroketals from assorted exocyclic enol ethers. Unlike conventional thermodynamic ketalization strategies, the stereochemical outcome for this approach is determined by a kinetic cycloaddition reaction. Thus, the stereochemical outcome reflects the olefin geometry of the starting materials along with the orientation of the associated transition state. However, the initial kinetic product can also be equilibrated by acid catalysis and reconstituted into a thermodynamic stereochemical arrangement. Thus, these strategies uniquely enable synthetic access to either the thermodynamic or kinetic conformation of the spiroketal stereocenter itself. Applications of these strategies in the syntheses of berkelic acid, β-rubromycin, and paecilospirone are presented along with the use of a chroman spiroketal for the construction of heliespirones A and C.

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Section: Resultsmentioning

confidence: 99%

New strategies for natural products containing chroman spiroketals

Green

Burnett

Pettus

2012

Pure and Applied Chemistry

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“…Apart from their involvement in biological processes, o ‐QMs are also very versatile intermediates in organic synthesis [119–124], but until now they have been less utilized in total syntheses [125]. Since they are ephemeral species [126], they must be generated in situ by processes that involve photolysis of o ‐, m ‐, or p ‐hydroxybenzyl alcohols [127], thermal reactions [128, 129], thermal extrusion of sulfur dioxide [128] and anionic triggered reactions [130, 131]. In this regard, Amouri et al .…”

Section: O‐quinone Methides: Generalitymentioning

confidence: 99%

Syntheses of chromenes and chromanes via o‐quinone methide intermediates

Ferreira

Silva

Pinto

et al. 2009

Journal of Heterocyclic Chem

126

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“…There are many methods to generate quinone methides, and some of reviews and articles have reported through some traditional forceful methods to generation of quinone methide [3,23]. This paper intends to review some recently developed and useful methods to produce quinone methide intermediates.…”

Section: Formation Of Quinone Methidementioning

confidence: 99%

Quinone Methide Derivatives: Important Intermediates to DNA Alkylating and DNA Cross-linking Actions

Wang

Song²,

Zhang³

et al. 2005

CMC

115

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Induced DNA interstrand cross-links by chemical agents or photoactivation play very important roles for cancer therapy. Several important clinical drugs (e.g. cisplatin, psoralens, and mitomycin C) are known to induce DNA ISC formation, which can disrupt cell maintenance and replication. Among these anti-tumor agents, one mechanism was involved in quinone methide intermediate. Quinone methide derivative has played important roles in organic syntheses as well as in chemical and biological processes. This review is concerned with current efforts of quinone methide derivatives to DNA alkylation and DNA cross-links. The latest advances in this field will be reviewed in this article. The chemical and physical properties of quinone methide derivatives, the interactions between nucleobases and quinone methide derivatives, the reactions with phosphodiester, DNA alkylation and cross-link via quinone methide intermediate action will be discussed.

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A Mild Anionic Method for Generating o-Quinone Methides: Facile Preparations of Ortho-Functionalized Phenols

Abstract: A low-temperature method for generating o-quinone methides is described which permits facile introduction of assorted R substituents onto the aryl ring system at low temperature. The method is useful for the efficient preparation of ortho-ring-alkylated phenols.

Cited by 47 publications

References 10 publications

New strategies for natural products containing chroman spiroketals

New strategies for natural products containing chroman spiroketals

Syntheses of chromenes and chromanes via o‐quinone methide intermediates

Quinone Methide Derivatives: Important Intermediates to DNA Alkylating and DNA Cross-linking Actions

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