Research

Exploring the Thioure​a Ligand in Pauson-Khand Reaction: A Powerful Tool for Natural Product Synthesis

Xinyu Tan, Zhilin Song, Xinting Liang, Zhenbao Wang, Hongyi Yuan, Zhongchao Zhang,*and Zhen Yang*

The Pauson-Khand (PK) reaction is one of the most efficient methods for constructing cyclopentenones, which are key frameworks in many natural products. Our group has also developed synthetic strategies to access biologically active complex natural products while searching for methods to enhance the efficiency of Pauson-Khand (PK) reactions. We identified Co2(CO)8/tetramethyl thiourea (TMTU) as a new catalyst that facilitates PK reactions under balloon pressure of CO at 70 °C (Org. Lett. 2005, 7, 593−595). Furthermore, we explored the first Pd-catalyzed PK reaction. The application of these PK reactions as key steps has enabled us to achieve the total synthesis of a range of complex natural products (Eur. J. Org. Chem. 2016, 2356−2368; Acc. Chem. Res. 2021, 54, 556−568), as well as by other groups (Synthesis 2014, 46, 2007−2023).