Convergent Formal Synthesis of (±)-Roseophilin

Convergent Formal Synthesis of (±)-Roseophilin

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.

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Veröffentlicht in:Journal of organic chemistry 2012-01, Vol.77 (1), p.704-706
Hauptverfasser: Song, Chuanjun, Liu, Hui, Hong, Meiling, Liu, Yuanyuan, Jia, Feifei, Sun, Li, Pan, Zhenliang, Chang, Junbiao
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic Compounds, 3-Ring - chemical synthesis
Heterocyclic Compounds, 3-Ring - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Pyrroles - chemical synthesis
Pyrroles - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo201949x