Abstract
The desymmetrization of p-peroxyquinols using a Brønsted acid-catalyzed acetalization/oxa-Michael cascade was achieved in high yields and selectivities for a variety of aliphatic and aryl aldehydes. Mechanistic studies suggest that the reaction proceeds through a dynamic kinetic resolution of the peroxy hemiacetal intermediate. The resulting 1,2,4-trioxane products were derivatized and show potent cancer cell-growth inhibition.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Acids / chemistry
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology
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Catalysis
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Cell Line, Tumor
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Cell Survival / drug effects
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Heterocyclic Compounds / chemical synthesis*
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Heterocyclic Compounds / chemistry
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Heterocyclic Compounds / pharmacology
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Humans
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Neoplasms / drug therapy
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Oxyquinoline / chemical synthesis
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Oxyquinoline / chemistry*
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Stereoisomerism
Substances
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1,2,4-trioxane
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Acids
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Antineoplastic Agents
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Heterocyclic Compounds
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Oxyquinoline