Open AccessDirect Synthesis of Stereodefined and Functionalized Dienes as Valuable Building Blocks
Author(s) -
Nuno Maulide,
Caroline Souris,
Frédéric Frébault,
Marco Luparia,
Davide Audisio
Publication year - 2014
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2014.248
Subject(s) - domino , stereoselectivity , chemistry , nucleophile , combinatorial chemistry , halide , allylic rearrangement , alkylation , natural product , bicyclic molecule , ring (chemistry) , tsuji–trost reaction , nucleophilic substitution , organic chemistry , catalysis
We have reported a direct and stereoselective synthesis of functionalized dienoic carboxylates from the simple bicyclic lactone 1. The use of oxygen- or nitrogen-based nucleophiles in a domino allylic alkylation/4?-electrocyclic ring opening affords reliable access to dienes with interesting functionalities. Alternatively, halide substitution offers synthesis of other classes of functionalized dienoic acids. Herein, we demonstrate the utility of such dienoic products as key building blocks in various transformations as well as natural product synthesis.