Organic Letters
Organic Letters
5 years ago

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

Bioinspired Total Synthesis of (±)-Chaetophenol C Enabled by a Pd-Catalyzed Cascade Cyclization
Hongbin Zhai, Bin Cheng, Yun Li, Hongyu Wang, Qingyu Zhang
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02124

DOI: 10.1021/acs.orglett.7b02124

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