Journal ArticleDOI
Diels–Alder trapping of in situ generated dienes from 3,4-dihydro-2H-pyran with p-quinone catalysed by p-toluenesulfonic acid
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This comprehensive study portrays that p-toluenesulfonic acid is a more efficient catalyst for the reaction between p-quinones and 3,4-dihydro-2H-pyran, than the Lewis acids.Abstract:
This comprehensive study portrays that p-toluenesulfonic acid is a more efficient catalyst for the reaction between p-quinones and 3,4-dihydro-2H-pyran, than the Lewis acids. The products were accomplished by the Diels–Alder cycloaddition reaction and their mechanistic pathways have been formulated. The impact of C2 and C2,5 substituents of the p-quinones on the cycloaddition reaction has been explored. Remarkably, it is the first report to explore this kind of in situ generated diene for the Diels–Alder cycloaddition reaction.read more
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Enantioselective Redox-Divergent Chiral Phosphoric Acid Catalyzed Quinone Diels–Alder Reactions
Thomas Varlet,Coralie Gelis,Pascal Retailleau,Guillaume Bernadat,Luc Neuville,Géraldine Masson +5 more
TL;DR: In this paper, an efficient enantioselective construction of tetrahydronaphthalene-1,4-diones as well as dihydronaphthalene 1,4diols by a chiral phosphoric acid catalyzed quinone Diels-Alder reaction with dienecarbamates is reported.
Journal ArticleDOI
1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones.
TL;DR: Pro-aromatic and volatile 1-methyl-1,4-cyclohexadiene (MeCHD) was used for the first time as a valid H-atom source in an innovative method to reduce ortho or para quinones to obtain the corresponding catechols and hydroquinones in good to excellent yields.
Journal ArticleDOI
Redox‐Divergent Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal Quinone Diels–Alder Reactions
Journal ArticleDOI
9,10-syn-podocarpane diterpenoids. An approach to the tricyclic skeleton by Diels-Alder cycloaddition: related crystal structure determination and theoretical aspects
TL;DR: In this article, a tricyclique de structure voisine de celle des precurseurs des podocarpanes, par cycloaddition du vinylcyclohexene avec l'acide benzoquinone-1,4 carboxylique, is presented.
References
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Journal ArticleDOI
Angiogenesis Inhibitor Epoxyquinol A: Total Synthesis and Inhibition of Transcription Factor NF-κB
TL;DR: The asymmetric synthesis of the natural product (+)-epoxyquinol A and related epoxyquinoid dimers, employing a cascade oxidation/electrocyclization/Diels-Alder dimerization sequence, is reported and it is shown that 1 and related molecules inhibit activation of the transcription factor NF-kappaB.
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Efficient total syntheses of (-)-colombiasin A and (-)-elisapterosin B: application of the Cr-catalyzed asymmetric quinone Diels-Alder reaction.
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Synthesis and antitumoral activities of marine ent-chromazonarol and related compounds.
TL;DR: Efficient syntheses of ent-isozonarol, 6a, 7a and 7a show a significative antitumoral activity and ent-chromazonarol from (-)-sclareol is described.
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Total synthesis of the novel, biologically active epoxyquinone dimer (+/-)-torreyanic acid: a biomimetic approach.
TL;DR: A total synthesis of the complex, biologically active, dimeric natural product (+/-)-torreyanic acid, which is composed of seven rings and laced with dense, variegated oxy-functionalization, has been accomplished from readily available allyl-substituted p-benzoquinone 8.
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Total synthesis of the novel angiogenesis inhibitors epoxyquinols A and B
Goverdhan Mehta,Kabirul Islam +1 more
TL;DR: The synthesis of the recently discovered angiogenesis inhibitors epoxyquinols A and B, having novel polyketide derived dimeric structures, has been accomplished from the readily available Diels-Alder adduct of cyclopentadiene and p-benzoquinone through a short, simple and flexible strategy as discussed by the authors.