Substituents Regulate the Cyclization of Conjugated Alkynes to Accurately Construct Cyclo-(<i>E</i>)-[3]dendralenes
Yun-Tao Xia,
Ya-Xin Li,
Tong-Tong Bi,
Wei Lian,
Xia Wang,
Meng Yan,
Tao Guo
Affiliations
Yun-Tao Xia
College of Chemistry & Chemical Engineering, Henan University of Technology, Academician Workstation for Natural Medicinal Chemistry of Henan Province, Zhengzhou 450001, China
Ya-Xin Li
College of Chemistry & Chemical Engineering, Henan University of Technology, Academician Workstation for Natural Medicinal Chemistry of Henan Province, Zhengzhou 450001, China
Tong-Tong Bi
College of Chemistry & Chemical Engineering, Henan University of Technology, Academician Workstation for Natural Medicinal Chemistry of Henan Province, Zhengzhou 450001, China
Wei Lian
College of Chemistry & Chemical Engineering, Henan University of Technology, Academician Workstation for Natural Medicinal Chemistry of Henan Province, Zhengzhou 450001, China
Xia Wang
College of Chemistry & Chemical Engineering, Henan University of Technology, Academician Workstation for Natural Medicinal Chemistry of Henan Province, Zhengzhou 450001, China
Meng Yan
College of Chemistry & Chemical Engineering, Henan University of Technology, Academician Workstation for Natural Medicinal Chemistry of Henan Province, Zhengzhou 450001, China
Tao Guo
College of Chemistry & Chemical Engineering, Henan University of Technology, Academician Workstation for Natural Medicinal Chemistry of Henan Province, Zhengzhou 450001, China
Substituent-regulated cyclization of conjugated alkynes with acid catalysis was developed in this paper, and it provides a straightforward synthesis of cyclic-(E)-[3]dendralenes. Depending on the electronic effect of the aromatic ring pairing, a variety of phosphinyl quintuplet/hexa cyclo-[3]dendralenes with diverse substitution patterns are accessible, with good efficiency and high stereoselectivity. This self-cyclization process achieves the first precise construction of a phosphinylcyclo-(E)-[3]dendralene from conjugated alkynes to aromatization.
