Catalytic Enantioselective Total Synthesis of Riccardiphenol B

Article Article scientifique Article Catalytic Enantioselective Total Synthesis of Riccardiphenol B eng 2016 author Cottet Pierre 733491 author Bleschke Christian Alexander 764001 author Guiteras Capdevila Montserrat 802300 author Tissot Matthieu 133733 author Alexakis Alexandre 123950 417-425 10.1002/adsc.201500928 1615-4150 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. Asymmetric catalysis Enolate trapping Michael addition Quaternary stereocenters Riccardiphenol B Sesquiterpenes Total synthesis Dewey 540 36 Département de chimie organique 141 false 759 Groupe Alexakis Advanced synthesis & catalysis 358 3 a33988e2-8d4e-4f75-9dba-c25f07a78539 Article (Published version) Restricted Cottet_et_al-2016-Advanced_Synthesis_&_Catalysis.pdf 497806 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Catalytic Enantioselective Total Synthesis of Riccardiphenol B	Advanced synthesis & catalysis			2016	838	3

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Guiteras Capdevila, Montserrat