'One-pot'four-step synthesis of cerpegin

J Lazaar, C Hoarau, F Mongin, F Trécourt, A Godard…

Index: Lazaar, Jalal; Hoarau, Christophe; Mongin, Florence; Trecourt, Francois; Godard, Alain; Queguiner, Guy; Marsais, Francis Tetrahedron Letters, 2005 , vol. 46, # 22 p. 3811 - 3813

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Citation Number: 21

Abstract

Cerpegin () was synthesized through a 'one-pot'reaction in 71% overall yield. Lithiation of commercially available 2-methoxynicotinic acid () as its lithium salt using LTMP, followed by addition of acetone at low temperature and a specific acidic treatment of the intermediate thus obtained, gave the 1, 1-dimethyl-3, 4-dioxo-1, 3, 4, 5-tetrahydrofuro [3, 4-c] pyridine (). The latter was finally selectively alkylated using methyl iodide and caesium carbonate to ...