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Enantioselective Palladium-Catalyzed Dearomative Cyclization for the Efficient Synthesis of Terpenes and Steroids
Ist Teil von
Angewandte Chemie (International ed.), 2015-03, Vol.54 (10), p.3033-3037
Auflage
International ed. in English
Ort / Verlag
Weinheim: WILEY-VCH Verlag
Erscheinungsjahr
2015
Quelle
MEDLINE
Beschreibungen/Notizen
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.
One, two, three: An enantioselective palladium‐catalyzed dearomative cyclization was developed for the efficient construction of a series of chiral tricyclic phenanthrenone derivatives bearing all‐carbon quaternary centers. This method was applied in highly efficient syntheses of a kaurene intermediate, the skeleton of the anabolic steroid boldenone, and the antimicrobial diterpene (−)‐totaradiol.