title: Asymmetric Syntheses of the Flavonoid Diels-Alder Natural Products Sanggenons C and O.
abstract: Metal-catalyzed, double Claisen rearrangement of a bis-allyloxyflavone has been utilized to enable a concise synthesis of the hydrobenzofuro[3,2-b]chromenone core structure of the natural products sanggenon A and sanggenol F. In addition, catalytic, enantioselective [4+2] cycloadditions of 2'-hydroxychalcones have been accomplished using B(OPh)3/BINOL complexes. Asymmetric syntheses of the flavonoid Diels-Alder natural products sanggenons C and O have been achieved employing a stereodivergent reaction of a racemic mixture (stereodivergent RRM) involving [4+2] cycloaddition.
authors.affiliation: Department of Chemistry and Center for Molecular Discovery (BU-CMD), Boston University , Boston, Massachusetts 02215, United States.
authors.forename: Chao
authors.initials: C
authors.lastname: Qi
authors.affiliation: Department of Chemistry and Center for Molecular Discovery (BU-CMD), Boston University , Boston, Massachusetts 02215, United States.
authors.forename: Yuan
authors.initials: Y
authors.lastname: Xiong
authors.affiliation: Department of Chemistry and Center for Molecular Discovery (BU-CMD), Boston University , Boston, Massachusetts 02215, United States.
authors.forename: Vincent
authors.initials: V
authors.lastname: Eschenbrenner-Lux
authors.affiliation: Department of Chemistry and Center for Molecular Discovery (BU-CMD), Boston University , Boston, Massachusetts 02215, United States.
authors.forename: Huan
authors.initials: H
authors.lastname: Cong
authors.affiliation: Department of Chemistry and Center for Molecular Discovery (BU-CMD), Boston University , Boston, Massachusetts 02215, United States.
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D005419:Flavonoids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D001572:Benzofurans; D001688:Biological Products; D002867:Chromones; D005419:Flavonoids; C000611642:sanggenon O; C477157:sanggenone C