Phosphoric Acid Catalyzed Desymmetrization of Bicyclic Bislactones Bearing an All‐Carbon Stereogenic Center: Total Syntheses of (−)‐Rhazinilam and (−)‐Leucomidine B |
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| Authors: | Jean‐Baptiste Gualtierotti Delphine Pasche Dr. Qian Wang Prof. Dr. Jieping Zhu |
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| Affiliation: | Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL‐SB‐ISIC‐LSPN, BCH 5304. 1015 Lausanne (Switzerland) http://lspn.epfl.ch |
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| Abstract: | In 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 monoacids 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. |
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| Keywords: | alkaloids natural products organocatalysis synthetic methods total synthesis |
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