Enantioselective photocycloaddition mediated by chiral Brønsted acids: asymmetric synthesis of the rocaglamides.
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.
Gerard
Baudouin
B
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, USA.
Sangji
Sheharbano
S
O'Leary
Daniel J
DJ
Porco
John A
JA
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
D000143:Acids; D001572:Benzofurans; C107772:rocaglamide