title: An oxidopyrylium cyclization/ring-opening route to polysubstituted α-hydroxytropolones.
abstract: α-Hydroxytropolones are a class of molecules with therapeutic potential against several human diseases. However, structure-activity relationship studies on these molecules have been limited due to a scarcity of efficient synthetic methods to access them. It is demonstrated herein that α-hydroxytropolones can be generated through a BCl(3)-mediated ring-opening/aromatization/demethylation process on 8-oxabicyclo[3.2.1]octenes. Used in conjunction with an improved method based on established oxidopyrylium dipolar cycloadditions, several polysubstituted α-hydroxytropolones can be accessed in three steps from readily available α-hydroxy-γ-pyrones.
authors.affiliation: Department of Chemistry, Brooklyn College, The City University of New York, Brooklyn, New York 11210, USA.
authors.forename: Christine
authors.initials: C
authors.lastname: Meck
authors.forename: Noushad
authors.initials: N
authors.lastname: Mohd
authors.forename: Ryan P
authors.initials: RP
authors.lastname: Murelli
mesh_terms: D003500:Cyclization; D006801:Humans; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014334:Tropolone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D014334:Tropolone