title: Enantioselective total synthesis and biological evaluation of (+)-kibdelone A and a tetrahydroxanthone analogue.
abstract: The total synthesis of kibdelone A has been accomplished via In(III)-catalyzed arylation of a heterocyclic quinone monoketal and iodine-mediated oxidative photochemical electrocyclization for construction of the ABCD ring moiety. Enzymatic dihydroxylation of methyl 2-halobenzoate substrates was employed for synthesis of activated 2-halo-cyclohexene F-ring fragments. A one pot oxa-Michael/Friedel-Crafts process allowed access to the first simplified DEF ring analogues of the kibdelones.
authors.affiliation: Department of Chemistry, Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
authors.forename: Dana K
authors.initials: DK
authors.lastname: Winter
authors.forename: Mary Ann
authors.initials: MA
authors.lastname: Endoma-Arias
authors.forename: Tomas
authors.initials: T
authors.lastname: Hudlicky
authors.forename: John A
authors.initials: JA
authors.lastname: Beutler
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003500:Cyclization; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007204:Indium / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D011809:Quinones / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D044004:Xanthones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D011809:Quinones; D044004:Xanthones; C586495:kibdelone A; D007204:Indium; D007455:Iodine