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Synthesis 2010(10): 1707-1711  
DOI: 10.1055/s-0029-1218735
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

The Meldrum’s Acid Route to Prodigiosin Analogues

Gordon A. Hunter, Hamish McNab*, Kirsti Withell
School of Chemistry, The University of Edinburgh, West Mains Road, Edinburgh EH9 3JJ, UK
Fax: +44(131)6504743; e-Mail: H.McNab@ed.ac.uk;
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Publication History

Received 15 February 2010
Publication Date:
09 April 2010 (online)

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Abstract

3-Methoxy-5-(2-thienyl)thiophene-2-carboxaldehyde and 3-methoxy-l-methyl-5-(2-thienyl)pyrrole-2-carboxaldehyde were prepared from the appropriate 3-hydroxypyrrole or 3-hydroxy­thiophene by regioselective O-alkylation and formylation. Condensation of these aldehydes with activated pyrroles in the presence of phosphoryl chloride provides analogues of prodigiosin, which differ from the natural products in the nature of the heteroatoms.

Key words

gas-phase reactions - heterocycles - pyrroles - prodigiosins

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