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Synthesis 2012; 44(21): 3321-3326
DOI: 10.1055/s-0032-1317351
DOI: 10.1055/s-0032-1317351
paper
A Paal–Knorr Approach to 3,4-Diaryl-Substituted Pyrroles: Facile Synthesis of Lamellarins O and Q
Weitere Informationen
Publikationsverlauf
Received: 11. Juni 2012
Accepted after revision: 14. September 2012
Publikationsdatum:
28. September 2012 (online)
Abstract
A very simple, yet efficient synthetic methodology, to obtain 3,4-diaryl-substituted pyrroles is described. The approach is based on the Knoevenagel condensation between arylacetonitriles and substituted aromatic aldehydes, followed by conjugate addition of cyanide to afford succinonitriles in excellent yields. The products thus obtained were subjected to DIBAL-H reduction, followed by cyclization under acidic conditions to produce the corresponding pyrroles in good overall yields. The utility of this protocol is exemplified by the synthesis of the marine alkaloids lamellarins O and Q.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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