Highly Enantioselective Tandem Michael Addition of Tryptamine-Derived Oxindoles to Alkynones: Concise Synthesis of Strychnos Alkaloids
Highly Enantioselective Tandem Michael Addition of Tryptamine-Derived Oxindoles to Alkynones: Concise Synthesis of Strychnos Alkaloids
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色胺衍生的羟吲哚与炔酮的高度对映选择性串联迈克尔加成：马钱子生物碱的简明合成
DOI：
10.1002/anie.201800567
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发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Xie Weiqing
中科院分区：
文献类型：
--
作者：
He Weigang;Hu Jiadong;Wang Pengyan;Chen Le;Ji Kai;Yang Siyu;Li Yin;Xie Zhilong;Xie Weiqing
利用手性N，N′-二氧化物Sc（OTf）3催化剂，发展了色胺衍生的羟吲哚与炔酮的高对映选择性串联Michael加成反应.该反应能够方便地合成对映体富集的螺[吡咯烷-3，3 ′-羟吲哚]化合物，为单萜吲哚生物碱的合成提供了一种新的策略.作为示范，马钱子生物碱[（-）-tubifoline，（-）-tubifolidine，（-）-dehydrotubifoline]的不对称合成在10-11个步骤中实现。
A highly enantioselective tandem Michael addition of tryptamine‐derived oxindoles to alkynones was developed by taking advantage of a chiralN,N′‐dioxide Sc(OTf)3catalyst. 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.