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Catalytic Enantioselective Total Synthesis of Riccardiphenol B

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Published in Advanced Synthesis and Catalysis. 2016, vol. 358, no. 3, p. 417-425
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 catalysisEnolate trappingMichael additionQuaternary stereocentersRiccardiphenol BSesquiterpenesTotal synthesis
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Other version: http://doi.wiley.com/10.1002/adsc.201500928
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Research group Groupe Alexakis
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COTTET, Pierre et al. Catalytic Enantioselective Total Synthesis of Riccardiphenol B. In: Advanced Synthesis and Catalysis, 2016, vol. 358, n° 3, p. 417-425. https://archive-ouverte.unige.ch/unige:80311

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Deposited on : 2016-02-03

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