Enantioselective photocycloaddition of 3-hydroxyflavones: total syntheses and absolute configuration assignments of (+)-ponapensin and (+)-elliptifoline.
We have previously reported development of biomimetic, asymmetric [3 + 2] photocycloadditions between 3-hydroxyflavones and cinnamate dipolarophiles to access (-)-rocaglamide and related natural products. Herein, we describe enantioselective syntheses of aglain cycloadducts leading to the first total syntheses and absolute configuration assignments of the aglain natural products (+)-ponapensin and (+)-elliptifoline.
Department of Chemistry, Center for Chemical Methodology and Library Development (CMLD-BU), Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
Neil J
NJ
Lajkiewicz
Stéphane P
SP
Roche
Baudouin
B
Gerard
John A
JA
Porco
D001572:Benzofurans / Q000737:chemistry; D005419:Flavonoids / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001572:Benzofurans; D005419:Flavonoids; D006575:Heterocyclic Compounds, 3-Ring; D011758:Pyrroles; C428176:elliptifoline; C483989:methyl rocaglate; C518999:ponapensin; C041477:3-hydroxyflavone