Oxa-enediynes: probing the electronic and stereoelectronic contributions to the Bergman cycloaromatization.
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).
Jones
Graham B
GB
Department of Chemistry, Northeastern University, Boston, Massachusetts 02115, USA. Gr.Jones@neu.edu
Wright
Justin M
JM
Hynd
George
G
Wyatt
Justin K
JK
Warner
Philip M
PM
Huber
Robert S
RS
Li
Aiwen
A
Kilgore
Michael W
MW
Sticca
Robert P
RP
Pollenz
Richard S
RS
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
D000480:Alkynes; D006573:Heterocyclic Compounds, 1-Ring; D006841:Hydrocarbons, Aromatic; D018336:Receptors, Aryl Hydrocarbon