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Catalytic Enantioselective Total Synthesis of Riccardiphenol B
Author(s) -
Cottet Pierre,
Bleschke Christian,
Capdevila Montse Guiteras,
Tissot Matthieu,
Alexakis Alexandre
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500928
Subject(s) - enantioselective synthesis , chemistry , stereocenter , total synthesis , conjugate , stereochemistry , catalysis , sesquiterpene , steric effects , enantiomer , derivative (finance) , combinatorial chemistry , organic chemistry , mathematical analysis , mathematics , financial economics , economics
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.