ortho-Quinone methides from para-quinones: total synthesis of rubioncolin B.
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.
Lumb
Jean-Philip
JP
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Choong
Kevin C
KC
Trauner
Dirk
D
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
D005663:Furans; D006873:Hydroquinones; D045563:Indolequinones; D009284:Naphthols; D010936:Plant Extracts; D011090:Polyenes; D011809:Quinones; C068040:quinone methide