title: Enantioselective photocycloaddition mediated by chiral Brønsted acids: asymmetric synthesis of the rocaglamides.
abstract: Enantioselective syntheses of methyl rocaglate and the related natural products rocaglamide and rocaglaol are outlined. The approach involves enantioselective [3 + 2] photocycloaddition promoted by chiral Brønsted acids (TADDOLs) to afford an aglain precursor followed by a ketol shift/reduction sequence to the rocaglate core.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, USA.
authors.forename: Baudouin
authors.initials: B
authors.lastname: Gerard
authors.forename: Sheharbano
authors.initials: S
authors.lastname: Sangji
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: O'Leary
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D000143:Acids / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis*; D029582:Meliaceae / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D010777:Photochemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013057:Spectrum Analysis; D013237:Stereoisomerism
chemical_list: D000143:Acids; D001572:Benzofurans; C107772:rocaglamide