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Enantioselective Photocycloaddition Mediated by Chiral Brønsted Acids:  Asymmetric Synthesis of the Rocaglamides

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journal contribution
posted on 21.06.2006, 00:00 by Baudouin Gerard, Sheharbano Sangji, Daniel J. O'Leary, John A. Porco
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.