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Divinylcarbinol Desymmetrization Strategy: A Concise and Reliable Approach to Chiral Hydroxylated Fatty Acid Derivatives.

Kenji SugimotoAmi KobayashiAki KohyamaHaruka SakaiYuji Matsuya
Published in: The Journal of organic chemistry (2021)
By the aid of the catalytic desymmetrization of divinylcarbinol as one-pot asymmetric induction and protection of olefin, asymmetric total syntheses of two chiral hydroxylated fatty acid derivatives were successfully achieved. The desired stereoisomers could be concisely prepared in mild conditions in a highly convergent manner. Thus, this novel strategy can help stereochemical elucidations of natural products, which have difficulties in spectroscopic stereochemical analyses due to their local symmetries in the vicinities of the stereogenic secondary hydroxyl units.
Keyphrases
  • fatty acid
  • capillary electrophoresis
  • ionic liquid
  • molecular docking
  • structure activity relationship
  • mass spectrometry