Phosphoric Acid Catalyzed Desymmetrization of Bicyclic Bislactones Bearing an All-Carbon Stereogenic Center: Total Syntheses of (−)-Rhazinilam and (−)-Leucomidine B

Gualtierotti, Jean-BaptistePasche, DelphineWang, QianZhu, Jieping2014-09-042014-09-042014-09-04201410.1002/anie.201405842https://infoscience.epfl.ch/handle/20.500.14299/106705WOS:000342678200044In the presence of a catalytic amount of an imidodiphosphoric acid, enantioselective desymmetrization of bicyclic bislactones by reaction with alcohols took place smoothly to afford enantiomerically enriched mono acids having an all-carbon stereogenic center. Concise catalytic enantioselective syntheses of both (-)-rhazinilam and (-)-leucomidine B were subsequently developed using (S)-methyl 4-ethyl-4-formylpimelate monoacid as a common starting material.alkaloidsnatural productsorganocatalysissynthetic methodstotal synthesisPhosphoric Acid Catalyzed Desymmetrization of Bicyclic Bislactones Bearing an All-Carbon Stereogenic Center: Total Syntheses of (−)-Rhazinilam and (−)-Leucomidine Btext::journal::journal article::research article