Enantioselective Palladium‐Catalyzed Dearomative Cyclization for the Efficient Synthesis of Terpenes and Steroids

Kang Du, Pan Guo, Yuan Chen, Zhen Cao, Zheng Wang, Wenjun Tang

Angewandte Chemie · 2015 · 49 citations · 74 references

Concepts

Abstract

Abstract A novel enantioselective palladium‐catalyzed dearomative cyclization has been developed for the efficient construction of a series of chiral phenanthrenone derivatives bearing an all‐carbon quaternary center. The effectiveness of this method in the synthesis of terpenes and steroids was demonstrated by a highly efficient synthesis of a kaurene intermediate, the facile construction of the skeleton of the anabolic steroid boldenone, and the enantioselective total synthesis of the antimicrobial diterpene natural product (−)‐totaradiol.

References

74