Development of the Claisen Rearrangement/Organocatalytic Diels-Alder Approach for the Synthesis of Eunicellins

被引：6

作者：

Hooper, Joel F. ^{[1
]}

White, Jonathan M. ^{[1
]}

Holmes, Andrew B. ^{[1
]}

机构：

[1] Univ Melbourne, Inst Bio21, Sch Chem, Parkville, Vic 3010, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2014年 / 67卷 / 8-9期

基金：

澳大利亚研究理事会;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; BRIAREUM-ASBESTINUM; GENERAL STRATEGY; NATURAL-PRODUCTS; OPHIRIN-B; DITERPENES; RING; ACETATE; (+)-VIGULARIOL;

D O I：

10.1071/CH14030

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The intramolecular Diels-Alder approach to synthesizing eunicellins has proved to be a powerful method for the synthesis of this class of natural products. The key to the success of this strategy is control over the endo/exo selectivity of the cycloaddition reaction, which we have addressed through an organocatalytic reaction employing the MacMillan imidazolidinone catalyst. This approach has been further developed to address the issue of functionality at the C8 position, and a novel scalable method for the extension of the medium-ring lactone has been developed.

引用

页码：1189 / 1194

页数：6

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