Bioinspired Total Synthesis of (±)-Chaetophenol C Enabled by a Pd-Catalyzed Cascade Cyclization

Yun Li; Qingyu Zhang; Hongyu Wang; Bin Cheng; Hongbin Zhai

doi:10.1021/acs.orglett.7b02124

Bioinspired Total Synthesis of (±)-Chaetophenol C Enabled by a Pd-Catalyzed Cascade Cyclization

Org Lett. 2017 Aug 18;19(16):4387-4390. doi: 10.1021/acs.orglett.7b02124. Epub 2017 Aug 7.

Authors

Yun Li^{1

2}, Qingyu Zhang¹, Hongyu Wang¹, Bin Cheng¹, Hongbin Zhai³

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, China.
² State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
³ Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University , Shenzhen 518055, China.

PMID: 28782961
DOI: 10.1021/acs.orglett.7b02124

Abstract

A novel Pd(II)-catalyzed cascade reaction has been developed that consists of a highly regio- and stereoselective oxa [4 + 2] cycloaddition reaction of o-alkynylbenzaldehydes and an intramolecular carboxylic group quenching of the in situ generated oxonium ion. This new reaction provides a one-step construction of the tetracyclic core structure of chaetophenol C from two simple starting materials. The developed chemistry was successfully applied to the first total synthesis of chaetophenol C and dozens of its analogues.

Publication types

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