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.

中文翻译：

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克林前列素的全效合成

报道了克林前列素的锅内经济合成，其中核心的双环[3.3.0]辛烯酮结构是通过两个关键步骤合成的：二苯基脯氨醇甲硅烷基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 ₂ NPh捕获生成的烯醇化物，随后利用Suzuki-Miyaura偶联反应。在七个罐中合成了手性非外消旋克林前列素，总收率为17％，对映选择性极好。