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

• Published in: Angewandte Chemie International Edition (ISSN: 1433-7851), vol. 53, num. 37, p. 9926-9930
• Weinheim: Wiley-Blackwell, 2014

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 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.

Keywords: alkaloids ; natural products ; organocatalysis ; synthetic methods ; total synthesis

Reference

• EPFL-ARTICLE-201573
• doi:10.1002/anie.201405842
• View record in Web of Science

Record created on 2014-09-04, modified on 2017-05-12