Direct Synthesis of Stereodefined and Functionalized Dienes as Valuable Building Blocks

被引：4

作者：

Maulide, Nuno ^{[1
]}

Souris, Caroline ^{[1
]}

Frebault, Frederic ^{[1
]}

Luparia, Marco ^{[1
]}

Audisio, Davide ^{[1
]}

机构：

[1] Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria

来源：

CHIMIA | 2014年 / 68卷 / 04期

关键词：

Allylic alkylation; Azide; Diene; Inthomycin C; Ring opening; CONROTATORY ELECTROCYCLIC REACTIONS; STEREOSELECTIVE-SYNTHESIS; DOMINO SYNTHESIS; CYCLOBUTENES; VERSATILE; ESTERS;

D O I：

10.2533/chimia.2014.248

中图分类号：

O6 [化学];

学科分类号：

0703 ;

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] .

引用

页码：248 / 251

页数：4

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