title: ortho-Quinone methides from para-quinones: total synthesis of rubioncolin B.
abstract: A concise synthesis of rubioncolin B is described, which features an unprecedented intramolecular Diels-Alder reaction involving an ortho-quinone methide and a naphthofuran moiety. The ortho-quinone methide is generated through a surprisingly facile tautomerization of a para-quinone.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Jean-Philip
authors.initials: JP
authors.lastname: Lumb
authors.forename: Kevin C
authors.initials: KC
authors.lastname: Choong
authors.forename: Dirk
authors.initials: D
authors.lastname: Trauner
mesh_terms: D019281:Dimerization; D005663:Furans / Q000737:chemistry; D006873:Hydroquinones / Q000138:chemical synthesis*; D045563:Indolequinones / Q000138:chemical synthesis*; D009284:Naphthols / Q000138:chemical synthesis*; D010936:Plant Extracts / Q000138:chemical synthesis; D011090:Polyenes / Q000737:chemistry; D011809:Quinones / Q000737:chemistry*; D045470:Rubia / Q000737:chemistry
chemical_list: D005663:Furans; D006873:Hydroquinones; D045563:Indolequinones; D009284:Naphthols; D010936:Plant Extracts; D011090:Polyenes; D011809:Quinones; C068040:quinone methide