Enantioselective photocycloaddition mediated by chiral Brønsted acids: Asymmetric synthesis of the rocaglamides

B Gerard, S Sangji, DJ O'Leary… - Journal of the American …, 2006 - ACS Publications
B Gerard, S Sangji, DJ O'Leary, JA Porco
Journal of the American Chemical Society, 2006ACS Publications
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.
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.
ACS Publications