Enantioselective synthesis of the bioactive flavanones lonchocarpol A and 6-(1,1-dimethylallyl)naringenin by catalytic asymmetric transfer hydrogenation

Research output: Contribution to journalResearch articleContributedpeer-review

Contributors

  • Morris Witt - , TUD Dresden University of Technology (Author)
  • Peter Metz - , TUD Dresden University of Technology (Author)

Abstract

Practical enantioselective syntheses of the natural products lonchocarpol A and 6-(1,1-dimethylallyl)naringenin as well as their optical antipodes are reported. A rhodium-catalyzed asymmetric transfer hydrogenation of readily available racemic substrates with virtually complete kinetic resolution served as the key step. Solvent-controlled, clay-catalyzed [1,3] or [3,3] shifts of prenyl aryl ethers were used to install the C-6 prenyl or 1,1-dimethylallyl substituent of the target flavanones.

Details

Original languageEnglish
Article number133719
JournalTetrahedron
Volume149
Publication statusPublished - 4 Dec 2023
Peer-reviewedYes

Keywords