Pot-Economical Total Synthesis of Clinprost
Pot-Economical Total Synthesis of Clinprost
复制标题
克林前列素的罐式经济全合成
DOI：
10.1021/acs.orglett.0c03616
复制
发表时间：
2020
期刊：
影响因子：
5.2
通讯作者：
Hayashi Yujiro
中科院分区：
文献类型：
--
作者：
Umekubo Nariyoshi;Hayashi Yujiro
报道了克林前列素的一锅经济合成法，其中双环[3.3.0]辛烯酮结构的核心通过两个关键步骤合成：二苯基脯氨醇硅醚催化的不对称多米诺Michael/Michael反应和分子内Horner-Wadsworth-Emmons反应。通过1，4-还原选择性地引入三取代的内环烯烃，然后用Tf 2NPh捕获所产生的烯醇化物，随后利用Suzuki-Miyaura偶联反应。手性，非外消旋克林前列素合成在七锅与17%的总收率和优良的对映体选择性。
The pot-economical synthesis of clinprost is reported, in which the core bicyclo[3.3.0]octenone structure was synthesized by two key steps: an asymmetric domino Michael/Michael reaction catalyzed by diphenylprolinol silyl ether and an intramolecular Horner–Wadsworth–Emmons reaction. The trisubstituted endocyclic alkene was selectively introduced by 1,4-reduction followed by trapping of the generated enolate with Tf2NPh and subsequent utilization of the Suzuki–Miyaura coupling reaction. Chiral, nonracemic clinprost was synthesized in seven pots with a 17% total yield and excellent enantioselectivity.