Catalytic asymmetric assembly of C3-monosubstituted chiral carbazolones and concise formal synthesis of (-)-aspidofractinine: application of enantioselective Pd-catalyzed decarboxylative protonation of carbazolones

Ruirui Zhao; Zhongwen Sun; Mingjie Mo; Fangzhi Peng; Zhihui Shao

doi:10.1021/ol501877x

Catalytic asymmetric assembly of C3-monosubstituted chiral carbazolones and concise formal synthesis of (-)-aspidofractinine: application of enantioselective Pd-catalyzed decarboxylative protonation of carbazolones

Org Lett. 2014 Aug 15;16(16):4178-81. doi: 10.1021/ol501877x. Epub 2014 Jul 25.

Authors

Ruirui Zhao¹, Zhongwen Sun, Mingjie Mo, Fangzhi Peng, Zhihui Shao

Affiliation

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

PMID: 25060656
DOI: 10.1021/ol501877x

Abstract

The first method for the asymmetric synthesis of C3-monosubstituted chiral carbazolones, structural motifs common in medicinal chemistry, has been achieved using Pd-catalyzed decarboxylative protonation of carbazolones. This methodology has been applied to the first catalytic enantioselective formal synthesis of (-)-aspidofractinine with step economy and simplicity.

Publication types

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

MeSH terms

Carbazoles / chemical synthesis*
Carbazoles / chemistry
Catalysis
Hydrogenation
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Molecular Structure
Palladium / chemistry*
Stereoisomerism

Substances

Carbazoles
Indole Alkaloids
aspidofractinine
Palladium