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手性催化的三环和四环螺环吲哚的不对称和发散合成:1,6-烯炔的可控区域选择性亲电卤环化反应

Catalytic Asymmetric and Divergent Synthesis of Tricyclic and Tetracyclic Spirooxindoles: Controllable Site-Selective Electrophilic Halocyclization of 1,6-Enynes.

机构信息

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology , Yunnan University , Kunming 650091 , China.

出版信息

Org Lett. 2019 Aug 2;21(15):6068-6073. doi: 10.1021/acs.orglett.9b02202. Epub 2019 Jul 18.

Abstract

Catalytic asymmetric and divergent assembly of tricyclic and tetracyclic 3,3'-pyrrolidonyl spirooxindoles was developed, involving a one-pot chiral Brønsted base catalyzed asymmetric propargylation for the synthesis of oxindole 1,6-enynes and a subsequent switchable site-selective and highly diastereoselective electrophilic iodocyclization of 1,6-enynes. In addition, antitumor properties of the newly synthesized compounds were evaluated.

摘要

发展了三环状和四环状 3,3'-吡咯烷二酮螺[吲哚啉-2,3'-吡咯]的催化不对称和发散性组装,涉及一锅手性 Brønsted 碱催化不对称炔丙基化以合成吲哚啉 1,6-二炔和随后的可切换的位点选择性和高非对映选择性的亲电碘环化 1,6-二炔。此外,还评估了新合成化合物的抗肿瘤特性。

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