Biomimetic Enantioselective Total Synthesis of (−)-Petromindole,Organic Letters

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Biomimetic Enantioselective Total Synthesis of (−)-Petromindole
Organic Letters ( IF 4.9 ) Pub Date : 2018-01-16 00:00:00 , DOI: 10.1021/acs.orglett.7b03768
Dattatraya H. Dethe ₁ , Susanta Kumar Sau ₁

Affiliation

The first enantioselective total synthesis of (−)-petromindole, an architecturally distinct congener of indole diterpene family, has been achieved. Key features of this synthetic route include the scalable and concise synthesis of tricyclic allylic alcohol from enantiopure Wieland–Mischer ketone derivative, and TMSOTf-mediated, highly efficient biomimetic C-4 cyclization of indole derivative for the rapid construction of a hexacyclic skeleton of petromindole.

中文翻译：

（-）-Petromindole的仿生对映选择性全合成

已经实现了对-吲哚并吲哚的第一个对映选择性全合成反应，这是吲哚二萜家族在结构上独特的同类物。该合成路线的关键特征包括从对映纯Wieland-Mischer酮衍生物可扩展且简明的合成三环烯丙基醇，以及TMSOTf介导的吲哚衍生物的高效仿生C-4环化反应，可快速构建邻苯二酚的六环骨架。

更新日期：2018-01-16

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