title: An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.
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.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: David M
authors.initials: DM
authors.lastname: Rubush
authors.forename: Michelle A
authors.initials: MA
authors.lastname: Morges
authors.forename: Barbara J
authors.initials: BJ
authors.lastname: Rose
authors.forename: Douglas H
authors.initials: DH
authors.lastname: Thamm
authors.forename: Tomislav
authors.initials: T
authors.lastname: Rovis
mesh_terms: D000143:Acids / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy; D015125:Oxyquinoline / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C503429:1,2,4-trioxane; D000143:Acids; D000970:Antineoplastic Agents; D006571:Heterocyclic Compounds; D015125:Oxyquinoline