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A Stereoselective Synthesis of the ACE Inhibitor Trandolapril
Synlett ( IF 1.7 ) Pub Date : 2019-03-15 , DOI: 10.1055/s-0037-1612306
Slim Chiha , Matthias Spilles , Jörg-Martin Neudörfl , Hans-Günther Schmalz 1
Affiliation  

A conceptually novel and stereoselective synthesis of the enantiopure octahydroindole building block and its conversion into the ACE inhibitor trandolapril was achieved. Key steps include the α-allylation of a protected l -pyroglutamic acid derivative, a highly diastereoselective Hosomi–Sakurai reaction and a Ru-catalyzed ring-closing metathesis of a 4,5-diallylated proline. This way, the synthesis of trandolapril was efficiently achieved in 25% overall yield (12 steps).

中文翻译:

ACE抑制剂群多普利的立体选择性合成

实现了对映纯八氢吲哚结构单元的概念新颖和立体选择性合成,并将其转化为 ACE 抑制剂群多普利。关键步骤包括受保护的 l-焦谷氨酸衍生物的 α-烯丙基化、高度非对映选择性的 Hosomi-Sakurai 反应和 Ru 催化的 4,5-二烯丙基化脯氨酸的闭环复分解。这样,群多普利的合成以 25% 的总产率(12 步)有效实现。
更新日期:2019-03-15
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