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Applications of counter-current chromatography in organic synthesis purification of heterocyclic derivatives of lapachol.

Silva RS, Leitão GG, Brum TB, Lobato AP, Pinto Mdo C, Pinto AV

Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Bloco H, CCS, Rio de Janeiro, RJ, Brazil.

This work describes the application of counter-current chromatography (CCC) as a useful, fast and economic alternative for the isolation and purification of heterocyclic derivatives from lapachol and beta-lapachone, two naturally occurring compounds from Tabebuia species, and nor-beta-lapachone, a synthetic congener of lapachol. The discussed data comprise four examples of purification of synthetic reactions with different solvent systems - the mixture of the oxazole and the imidazole from beta-lapachone; the quinoxaline from nor-beta-lapachone; and the purification of the N-oxides from the quinoxaline and the phenazine from nor-beta-lapachone from their respective not fully reacted substrates by means of aqueous reversed- and normal-phase elution modes and non-aqueous solvent systems. Traditional purification of these reaction products by silica gel column chromatography demanded a large amount of solvent and time and, in some cases, serious degradation of the products occurred, leading to low yield of the reaction. High-speed counter-current chromatography (HSCCC) was used as an alternative to optimize the process and raise the yield of the reactions.

Published 9 May 2007 in J Chromatogr A, 1151(1): 197-202.
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