高对映选择性色胺衍生的吲哚酮与炔酮的串联迈克尔加成：士的宁生物碱的简洁合成。
Highly Enantioselective Tandem Michael Addition of Tryptamine-Derived Oxindoles to Alkynones: Concise Synthesis of Strychnos Alkaloids.
机构信息
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling, 712100, Shaanxi, China.
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Key Laboratory of Botanical Pesticide R&D in Shaanxi Province, Yangling, Shaanxi, 712100, China.
出版信息
Angew Chem Int Ed Engl. 2018 Mar 26;57(14):3806-3809. doi: 10.1002/anie.201800567. Epub 2018 Feb 28.
A highly enantioselective tandem Michael addition of tryptamine-derived oxindoles to alkynones was developed by taking advantage of a chiral N,N'-dioxide Sc(OTf) catalyst. The reaction enables the facile preparation of enantioenriched spiro[pyrrolidine-3,3'-oxindole] compounds, which provides a novel strategy for the synthesis of monoterpenoid indole alkaloids. As a demonstration, the asymmetric synthesis of strychnos alkaloids [(-)-tubifoline, (-)-tubifolidine, (-)-dehydrotubifoline] was achieved in 10-11 steps.
手性 N,N'-二氧化钪（Sc(OTf)）催化剂的应用使得吲哚酮与色胺衍生的氧化吲哚的高对映选择性串联迈克尔加成得以实现。该反应可轻松制备对映体富集的螺[吡咯烷-3,3'-吲哚]化合物，为单萜吲哚生物碱的合成提供了一种新策略。作为一个例证，通过 10-11 步反应实现了士的宁类生物碱[（-）-tubifoline、（-）-tubifolidine、（-）-dehydrotubifoline]的不对称合成。
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