Synthesis of the ABC ring system of Jiadifenin via Pd-catalyzed cyclizations.
An efficient route toward the central ABC system of jiadifenin has been developed using two key Pd-catalyzed cyclizations. A protic solvent-activated Mizoroki-Heck reaction was used to construct the C(9) quaternary carbon and the A ring. A cascading Tsuji-Trost cyclization/lactonization sequence was employed to establish the BC ring system and the C(5,6) stereochemistry.
Faculty of Parmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, Japan.
Kenichi
K
Harada
Akiko
A
Imai
Kazuharu
K
Uto
Rich G
RG
Carter
Miwa
M
Kubo
Hideaki
H
Hioki
Yoshiyasu
Y
Fukuyama
D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*
D012717:Sesquiterpenes; C457979:jiadifenin; D010165:Palladium