Direct Synthesis of Stereodefined and Functionalized Dienes as Valuable Building Blocks

作者:Maulide Nuno*; Souris Caroline; Frebault Frederic; Luparia Marco; Audisio Davide
来源:Chimia, 2014, 68(4): 248-251.
DOI:10.2533/chimia.2014.248

摘要

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 pi-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. [GRAPHICS] .

  • 出版日期2014