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

Taochun Zha; Xinyu Tong; Yuhua Deng; Fangzhi Peng; Zhihui Shao

doi:10.1021/acs.orglett.9b02202

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

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

Authors

Taochun Zha¹, Xinyu Tong¹, Yuhua Deng¹, Fangzhi Peng¹, Zhihui Shao¹

Affiliation

¹ Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology , Yunnan University , Kunming 650091 , China.

PMID: 31318558
DOI: 10.1021/acs.orglett.9b02202

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.

Publication types

Research Support, Non-U.S. Gov't