Atroposelective Construction of Nine-Membered Carbonate-Bridged Biaryls

Shiqi Jia; Yuhong Tian; Xin Li; Pengfei Wang; Yu Lan; Hailong Yan

doi:10.1002/anie.202206501

Atroposelective Construction of Nine-Membered Carbonate-Bridged Biaryls

Angew Chem Int Ed Engl. 2022 Aug 1;61(31):e202206501. doi: 10.1002/anie.202206501. Epub 2022 Jun 14.

Authors

Shiqi Jia¹, Yuhong Tian², Xin Li², Pengfei Wang², Yu Lan^{1

3}, Hailong Yan²

Affiliations

¹ Green Catalysis Center, and College of Chemistry, Zhengzhou University, 100 Science Avenue, Zhengzhou, 450001, Henan, P. R. China.
² Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing, 401331, P. R. China.
³ School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 401331, P. R. China.

PMID: 35621411
DOI: 10.1002/anie.202206501

Abstract

We herein demonstrated an efficient method for the atroposelective construction of nine-membered carbonate-bridged biaryls through vinylidene ortho-quinone methide (VQM) intermediates. Diverse products with desirable pharmacological features were synthesized in satisfying yields and good to excellent enantioselectivities. In subsequent bioassays, several agents showed considerable antiproliferative activity via the mitochondrial-related apoptosis mechanism. Further transformations produced more structural diversity and may inspire new ideas for developing functional molecules.

Keywords: Atroposelectivity; Bridged Biaryls; Enantioselectivity; Organocatalysis; Vinylidene ortho-Quinone Methide (VQM).

Publication types

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

MeSH terms

Carbonates*

Substances

Carbonates