环肽生物碱的高度汇聚合成路线：紫芝碱N的全合成

Highly convergent route to cyclopeptide alkaloids: total synthesis of ziziphine N.

作者信息

He Gang, Wang Jing, Ma Dawei

机构信息

State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, China.

出版信息

Org Lett. 2007 Mar 29;9(7):1367-9. doi: 10.1021/ol070271f. Epub 2007 Mar 9.

DOI:10.1021/ol070271f

PMID:17346058

Abstract

[structure: see text]. A highly convergent protocol to cyclopeptide alkaloids, as demonstrated by the first total synthesis of antiplasmodial agent ziziphine N, is developed. The key elements include construction of its aryl ether unit via Mitsunobu reaction, installation of its enamide part via CuI/N,N-dimethylglycine-catalyzed coupling reaction, and ring closure with coupling agents such as FDDP and DPPA.

摘要

[结构：见正文]。开发了一种高度汇聚的环肽生物碱合成方法，抗疟药酸枣碱N的首次全合成证明了该方法。关键步骤包括通过光延反应构建其芳基醚单元，通过碘化亚铜/N,N-二甲基甘氨酸催化的偶联反应安装其烯酰胺部分，以及使用诸如FDDP和DPPA等偶联剂进行环化。