Synthesis of Tetrahydropyran/Tetrahydrofuran-Containing Macrolides by Palladium-Catalyzed Alkoxycarbonylative Macrolactonizations

被引：51
作者：
Bai, Yu [1 ]
Davis, Dexter C. [1 ]
Dai, Mingji [1 ]
机构：
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 25期
关键词：
carbonylation; macrolactonization; macrolide; neopeltolide; palladium; ENANTIOSELECTIVE TOTAL-SYNTHESIS; DIVERSITY-ORIENTED SYNTHESIS; FORMAL TOTAL-SYNTHESIS; INTRAMOLECULAR CARBONYLATION; STEREOSELECTIVE-SYNTHESIS; COMPLEXED DENDRIMERS; STRUCTURAL REVISION; LEUCASCANDROLIDE-A; LYNGBYALOSIDE-B; NEOPELTOLIDE;
D O I：
10.1002/anie.201403006
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel Pd-catalyzed cascade alkoxycarbonylative macrolactonization to construct tetrahydropyran/ tetrahydrofuran-containing bridged macrolactones in one step from alkendiols is described. Products with various ring sizes and substituents were obtained. Challenging macrolactones involving tertiary alcohols were synthesized smoothly as well. Mechanistically, experimental evidence to support a transoxypalladation step has been provided. The method was applied to the synthesis of potent anticancer compound 9-demethylneopeltolide.
引用
收藏
页码：6519 / 6522
页数：4
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