Strategies for the Total Synthesis of C2-C11 Cyclized Cembranoids

被引：43

作者：

Ellis, J. Michael ^{[1
]}

Crimmins, Michael T. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA

来源：

CHEMICAL REVIEWS | 2008年 / 108卷 / 12期

关键词：

D O I：

10.1021/cr078117u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A number of strategies for the total synthesis of C2-C11 cyclized cembranoids were discussed. The C2-C11 cyclized cembranoids include the eunicellins, asbestinins are secondary metabolites isolated from gorgonian octocorals and soft corals. The first total synthesis of a C2-C11 hinges upon the formation of the hydroisobenzofuran functionality through a prins-pinacol condensation-rearrangement, employed for the stereoselective synthesis of tetrahydrofurans. The next extended Prins-pinacol condensation-rearrangement approach to a cladiellin of potential pharmocological utility. Each of the described synthesis have targeted cembranoids containing a (Z)-oxozene or lacking an endocyclic olefin within the nine-membered ring of the natural products. Diverse strategies can be found within the literature that approach these molecular skeletons.

引用

页码：5278 / 5298

页数：21

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