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Scientific article
English

Catalytic Enantioselective Total Synthesis of Riccardiphenol B

Published inAdvanced synthesis & catalysis, vol. 358, no. 3, p. 417-425
Publication date2016
Abstract

The first catalytic enantioselective total synthesis of riccardiphenol B, a sesquiterpene derivative isolated from a Japanese collection of the liverwort Riccardia crassa, has been achieved. A copper-catalyzed asymmetric conjugate addition of trimethylaluminum was used at an early stage to generate the quaternary stereogenic center with high enantiomeric excess. The corresponding sterically encumbered aluminum enolate was directly trapped with an α-amino ether, allowing after oxidation, the release of a key intermediate in the total synthesis of the target natural product.

Keywords
  • Asymmetric catalysis
  • Enolate trapping
  • Michael addition
  • Quaternary stereocenters
  • Riccardiphenol B
  • Sesquiterpenes
  • Total synthesis
Research group
Citation (ISO format)
COTTET, Pierre et al. Catalytic Enantioselective Total Synthesis of Riccardiphenol B. In: Advanced synthesis & catalysis, 2016, vol. 358, n° 3, p. 417–425. doi: 10.1002/adsc.201500928
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Article (Published version)
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Identifiers
ISSN of the journal1615-4150
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Technical informations

Creation02/02/2016 6:03:00 PM
First validation02/02/2016 6:03:00 PM
Update time03/15/2023 12:07:24 AM
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