title: Palladium-catalyzed sequential arylation and allylic alkylation of highly functionalized ketones: a concise synthesis of mesembrine.
abstract: 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.
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, PR China.
authors.forename: Yuanhong
authors.initials: Y
authors.lastname: Zhao
authors.forename: Yongyun
authors.initials: Y
authors.lastname: Zhou
authors.forename: Leilei
authors.initials: L
authors.lastname: Liang
authors.forename: Xiaodong
authors.initials: X
authors.lastname: Yang
authors.forename: Fengxiang
authors.initials: F
authors.lastname: Du
authors.forename: Liang
authors.initials: L
authors.lastname: Li
authors.forename: Hongbin
authors.initials: H
authors.lastname: Zhang
mesh_terms: 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*
chemical_list: D001688:Biological Products; D026121:Indole Alkaloids; D007659:Ketones; D010165:Palladium; C011300:mesembrine