Journal ArticleDOI
o-Quinone methides: intermediates underdeveloped and underutilized in organic synthesis
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This article is published in Tetrahedron.The article was published on 2002-07-01. It has received 492 citations till now. The article focuses on the topics: Organic synthesis & Benzopyrans.read more
Citations
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Cascade reactions in total synthesis.
TL;DR: The power of cascade reactions in total synthesis is illustrated in the construction of complex molecules and underscore their future potential in chemical synthesis.
Journal ArticleDOI
Kaskadenreaktionen in der Totalsynthese
Kyriacos C. Nicolaou,Kyriacos C. Nicolaou,David J. Edmonds,David J. Edmonds,Paul G. Bulger,Paul G. Bulger +5 more
TL;DR: In this article, ausgewahlte Kaskadenreaktionen in der Naturstoffsynthese erlautert, wobei neuere Anwendungen besonders hervorgehoben werden.
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Formal [4+1] Annulation Reactions in the Synthesis of Carbocyclic and Heterocyclic Systems
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The domestication of ortho-quinone methides.
Wen-Ju Bai,Jonathan G. David,Zhen-Gao Feng,Marisa G. Weaver,Kun-Liang Wu,Thomas R. R. Pettus +5 more
TL;DR: A mild anionic triggering procedure to generate transitory o-QMs at low temperature from readily available salicylaldehydes, particularly OBoc derivatives was discovered and this novel reaction cascade proved controllable through careful manipulation of metallic and temperature levers so that it could be paused, stopped, or restarted at various intermediates and stages.
Journal ArticleDOI
ortho‐Quinone Methides in Natural Product Synthesis
TL;DR: This review encompasses the major contributions inortho-Quinone methides, exemplifying the major strategies and reactivity modes which can be applied.
References
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Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics
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Origin of reactivity, regioselectivity, and periselectivity in 1,3-dipolar cycloadditions
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Heterodiene syntheses with .alpha.,.beta.-unsaturated carbonyl compounds
G. Desimoni,G. Tacconi +1 more
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Studies on the metabolism of troglitazone to reactive intermediates in vitro and in vivo. Evidence for novel biotransformation pathways involving quinone methide formation and thiazolidinedione ring scission.
Kelem Kassahun,Paul G. Pearson,Wei Tang,Ian McIntosh,Kwan Leung,Charles S. Elmore,Dennis C. Dean,Regina Wang,George Doss,Thomas A. Baillie +9 more
TL;DR: The finding that metabolism of the TZD ring of troglitazone was catalyzed selectively by P450 3A enzymes is significant in light of the recent report that trog litazone is an inducer of this isoform in human hepatocytes.