Palladium-catalyzed sequential arylation and allylic alkylation of highly functionalized ketones: a concise synthesis of mesembrine.
An unprecedented palladium-catalyzed sequential procedure toward arylation and allylic alkylation of highly functionalized cyclohexenones was developed. This new protocol leads to useful building blocks containing a benzylic quaternary carbon in only one step. A concise total synthesis of mesembrine based on this procedure was achieved in only five steps with 22% overall yield.
Zhao
Yuanhong
Y
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, PR China.
Zhou
Yongyun
Y
Liang
Leilei
L
Yang
Xiaodong
X
Du
Fengxiang
F
Li
Liang
L
Zhang
Hongbin
H
D000478:Alkylation; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
D001688:Biological Products; D026121:Indole Alkaloids; D007659:Ketones; D010165:Palladium; C011300:mesembrine