Cascade Claisen and Meinwald Rearrangement for One-Pot Divergent Synthesis of Benzofurans and 2 H-Chromenes

Liyan Song; Qian Su; Xi Lin; Zhihui Du; Huiyou Xu; Ming-An Ouyang; Hongliang Yao; Rongbiao Tong

doi:10.1021/acs.orglett.0c00770

Cascade Claisen and Meinwald Rearrangement for One-Pot Divergent Synthesis of Benzofurans and 2 H-Chromenes

Org Lett. 2020 Apr 17;22(8):3004-3009. doi: 10.1021/acs.orglett.0c00770. Epub 2020 Apr 3.

Authors

Liyan Song¹, Qian Su¹, Xi Lin¹, Zhihui Du¹, Huiyou Xu¹, Ming-An Ouyang¹, Hongliang Yao², Rongbiao Tong³

Affiliations

¹ Key Laboratory of Biopesticide and Chemical Biology (Ministry of Education), College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou, Fujian 350002, China.
² Guangdong Key Laboratory of Animal Conservation and Resource Utilization, Guangdong Public Laboratory of Wild Animal Conservation and Utilization, Drug Synthesis and Evaluation Center, Guangdong Institute of Applied Biological Resources, Guangzhou, Guangdong 510260, China.
³ Department of Chemistry, The Hong Kong University of Science and Technology, Clearwater Bay, Kowloon, Hong Kong, China.

PMID: 32242416
DOI: 10.1021/acs.orglett.0c00770

Abstract

A new cascade approach has been developed for the one-pot four-step divergent synthesis of polysubstituted benzofurans and 2H-chromenes, featuring a novel cascade aromatic Claisen rearrangement/Meinwald rearrangement/dehydrative or oxidative cyclization. This new method was demonstrated with 39 examples tolerating different substitutions at an epoxide, allylic ether, and aromatic ring, and we showcased its utility with the first total synthesis of natural product liparacid A in seven steps.

Publication types

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