One-Pot AgOAc-Mediated Synthesis of Polysubstituted Pyrroles from Primary Amines and Aldehydes: Application to the Total Synthesis of Purpurone

A simple and efficient method for the synthesis of 1,3,4-trisubstituted or 3,4-disubstituted pyrroles has been developed. The reaction represents the first time that pyrroles are synthesized directly from readily available aldehydes and amines (anilines) as starting materials. This method has been s...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 18; pp. 4066 - 4069
Main Authors Li, Qingjiang, Fan, Aili, Lu, Zhiyao, Cui, Yuxin, Lin, Wenhan, Jia, Yanxing
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.09.2010
Amer Chemical Soc
Subjects
Acetates - chemistry
Aldehydes - chemistry
Amines - chemistry
Chemistry
Chemistry, Organic
Dimerization
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Molecular Structure
Physical Sciences
Pyrroles - chemical synthesis
Science & Technology
Silver Compounds - chemistry
OXIDATION
ENAMINE-ESTERS
SEQUENTIAL REACTIONS
EFFICIENT TOTAL-SYNTHESIS
LEAD-TETRAACETATE
ALPHA-ARYLATION
C BOND FORMATION
SUBSTITUTED PYRROLES
DIRECT ANNULATION
ALKALOIDS
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Summary:A simple and efficient method for the synthesis of 1,3,4-trisubstituted or 3,4-disubstituted pyrroles has been developed. The reaction represents the first time that pyrroles are synthesized directly from readily available aldehydes and amines (anilines) as starting materials. This method has been successfully applied to the rapid synthesis of purpurone.
Bibliography:ObjectType-Article-1
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ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol101644g