Convergent formal synthesis of (±)-roseophilin

Chuanjun Song; Hui Liu; Meiling Hong; Yuanyuan Liu; Feifei Jia; Li Sun; Zhenliang Pan; Junbiao Chang

doi:10.1021/jo201949x

Convergent formal synthesis of (±)-roseophilin

J Org Chem. 2012 Jan 6;77(1):704-6. doi: 10.1021/jo201949x. Epub 2011 Nov 28.

Authors

Chuanjun Song¹, Hui Liu, Meiling Hong, Yuanyuan Liu, Feifei Jia, Li Sun, Zhenliang Pan, Junbiao Chang

Affiliation

¹ Department of Chemistry, Zhengzhou University, 100 Science Avenue, Zhengzhou, Henan Province 450001, PR China. chjsong@zzu.edu.cn

PMID: 22098172
DOI: 10.1021/jo201949x

Abstract

A facile convergent synthesis of the tricyclic core 2 of roseophilin is described, which represents the shortest route so far for the formal synthesis of roseophilin. The key step was a tandem pyrrole acylation-Nazarov cyclization reaction to form the cyclopenta[b]pyrrole moiety 4.

Publication types

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

MeSH terms

Catalysis
Cyclization
Heterocyclic Compounds, 3-Ring / chemical synthesis
Heterocyclic Compounds, 3-Ring / chemistry
Molecular Structure
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Stereoisomerism

Substances

Heterocyclic Compounds, 3-Ring
Pyrroles
roseophilin