title: Oxa-enediynes: probing the electronic and stereoelectronic contributions to the Bergman cycloaromatization.
abstract: Efficient routes to three classes of 10-membered oxa-enediynes are presented. The electronic and stereoelectronic contributions to half-lives are supported by density functional theory calculations. One member of this class cyclizes to give an isochroman which binds to and degrades the aryl hydrocarbon receptor (AhR).
authors.affiliation: Department of Chemistry, Northeastern University, Boston, Massachusetts 02115, USA. Gr.Jones@neu.edu
authors.forename: Graham B
authors.initials: GB
authors.lastname: Jones
authors.forename: Justin M
authors.initials: JM
authors.lastname: Wright
authors.forename: George
authors.initials: G
authors.lastname: Hynd
authors.forename: Justin K
authors.initials: JK
authors.lastname: Wyatt
authors.forename: Philip M
authors.initials: PM
authors.lastname: Warner
authors.forename: Robert S
authors.initials: RS
authors.lastname: Huber
authors.forename: Aiwen
authors.initials: A
authors.lastname: Li
authors.forename: Michael W
authors.initials: MW
authors.lastname: Kilgore
authors.forename: Robert P
authors.initials: RP
authors.lastname: Sticca
authors.forename: Richard S
authors.initials: RS
authors.lastname: Pollenz
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry / Q000493:pharmacokinetics; D000818:Animals; D002455:Cell Division / Q000187:drug effects; D002460:Cell Line; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis / Q000737:chemistry / Q000493:pharmacokinetics; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D018336:Receptors, Aryl Hydrocarbon / Q000378:metabolism*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000480:Alkynes; D006573:Heterocyclic Compounds, 1-Ring; D006841:Hydrocarbons, Aromatic; D018336:Receptors, Aryl Hydrocarbon