Bioinspired Total Synthesis of (±)-Chaetophenol C Enabled by a Pd-Catalyzed Cascade Cyclization
Yun Li1,2, Qingyu Zhang1, Hongyu Wang1
1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, China.
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.
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