Buffer-induced, selective mono-C-alkylation of phloroglucinol: application to the synthesis of an advanced intermediate of catechin
A Gissot, A Wagner, C Mioskowski
Index: Gissot, Arnaud; Wagner, Alain; Mioskowski, Charles Tetrahedron, 2004 , vol. 60, # 32 p. 6807 - 6812
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Citation Number: 7
Abstract
A straightforward mono-selective and C-specific alkylation of phloroglucinol with activated alkyl halides is presented. The use of water as solvent limits the amount of over-alkylated by- products. Provided some minor changes in the experimental conditions, hydrophobic cinnamyl halides can also be reacted, thus giving a direct access to advanced intermediates of natural flavonoids.
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[Lamidey, Anne-Marie; Fernon, Lionel; Pouysegu, Laurent; Delattre, Charlotte; Quideau, Stephane; Pardon, Patrick Helvetica Chimica Acta, 2002 , vol. 85, # 8 p. 2328 - 2334]