title: Enantioselective palladium-catalyzed dearomative cyclization for the efficient synthesis of terpenes and steroids.
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.
authors: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai 200032 (China).
authors: Kang
authors: K
authors: Du
authors: Pan
authors: P
authors: Guo
authors: Yuan
authors: Y
authors: Chen
authors: Zhen
authors: Z
authors: Cao
authors: Zheng
authors: Z
authors: Wang
authors: Wenjun
authors: W
authors: Tang
mesh_terms: D002384:Catalysis; D003500:Cyclization; D008958:Models, Molecular; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis*; D013729:Terpenes / Q000138:chemical synthesis*
chemical_list: D013256:Steroids; D013729:Terpenes; D010165:Palladium
keywords: asymmetric cyclization; palladium; phosphine ligands; total synthesis; transition-metal catalysis