title: Triflic acid-mediated rearrangements of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: synthesis of methoxytropolones and furans.
abstract: Methoxytropolones are useful scaffolds for therapeutic development because of their known biological activity and established value in the synthesis of α-hydroxytropolones. Upon treatment with triflic acid, a series of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones rearrange rapidly and cleanly to form methoxytropolones. Interestingly, bicycles that are derived from dimethyl acetylenedicarboxylate (R(2) = R(3) = CO2Me) instead form furans as the major product.
authors.affiliation: Department of Chemistry, Brooklyn College, The City University of New York , 2900 Bedford Avenue, Brooklyn, New York, 11210, United States.
authors.forename: Yvonne D
authors.initials: YD
authors.lastname: Williams
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: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D014334:Tropolone / Q000031:analogs & derivatives / Q000737:chemistry
chemical_list: C000592219:3-methoxy-8-oxabicyclo(3.2.1)octa-3,6-dien-2-one; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005663:Furans; D008698:Mesylates; C037100:2-methoxytropolone; D014334:Tropolone; C012077:trifluoromethanesulfonic acid