Palladium-catalyzed sequential arylation and allylic alkylation of highly functionalized ketones: a concise synthesis of mesembrine

Yuanhong Zhao; Yongyun Zhou; Leilei Liang; Xiaodong Yang; Fengxiang Du; Liang Li; Hongbin Zhang

doi:10.1021/ol802608r

Palladium-catalyzed sequential arylation and allylic alkylation of highly functionalized ketones: a concise synthesis of mesembrine

Org Lett. 2009 Feb 5;11(3):555-8. doi: 10.1021/ol802608r.

Authors

Yuanhong Zhao¹, Yongyun Zhou, Leilei Liang, Xiaodong Yang, Fengxiang Du, Liang Li, Hongbin Zhang

Affiliation

¹ Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, PR China.

PMID: 19117400
DOI: 10.1021/ol802608r

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Biological Products / chemical synthesis*
Biological Products / chemistry
Catalysis
Combinatorial Chemistry Techniques
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Ketones / chemistry*
Molecular Structure
Palladium / chemistry*

Substances

Biological Products
Indole Alkaloids
Ketones
Palladium
mesembrine