克沙米星A的全合成

Total synthesis of crisamicin A.

作者信息

Li Zhengtao, Gao Yingxiang, Tang Yefeng, Dai Mingji, Wang Guoxin, Wang Zhigang, Yang Zhen

机构信息

Laboratory of Chemical Genomics, Shenzhen Graduate School, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing.

出版信息

Org Lett. 2008 Jul 17;10(14):3017-20. doi: 10.1021/ol800977n. Epub 2008 Jun 14.

DOI:10.1021/ol800977n

PMID:18553973

Abstract

Stereoselective total synthesis of natural product crisamicin A (1) was accomplished for the first time via the Pd/TMTU-catalyzed alkoxycarbonylative annulation to generate a unique cis-pyran-fused lactone, an intermolecular Diels-Alder reaction to construct the pyranonaphthoquinone unit, and a novel Pd-thiourea pincer complex-catalyzed homocoupling of functionalized naphthoquinones.

摘要

首次通过钯/四甲基硫脲催化的烷氧基羰基化环化反应生成独特的顺式吡喃并内酯、分子间狄尔斯-阿尔德反应构建吡喃萘醌单元以及新型钯-硫脲钳形配合物催化的官能化萘醌的均偶联反应，完成了天然产物crisamicin A（1）的立体选择性全合成。