Premium
Enantioselective Palladium‐Catalyzed Dearomative Cyclization for the Efficient Synthesis of Terpenes and Steroids
Author(s) -
Du Kang,
Guo Pan,
Chen Yuan,
Cao Zhen,
Wang Zheng,
Tang Wenjun
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201411817
Subject(s) - enantioselective synthesis , chemistry , terpene , palladium , catalysis , organic chemistry , combinatorial chemistry , total synthesis , quaternary carbon , diterpene
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.