查看文章

The present short review focus on chemical transformations of lapachol to a larae number of biogenetically related lapachol conegeners, dlmers and heterocyclic analogues that have been achieved in our laboratory during more than two decades. Conversion of lapachol to stenoearpoquinone-B, rhinaeanthin-A, Jl-(1-hydroxyisopropanyl)-dihydrofurano-1, 2-naphthoqulnone, stenocarpoqulnone-A, dehydro-a-lapachone and dehydro-JI-iapachone by the reaction with m-ehloroperbenzoic acid; dehydrolso-a-lapachone, dehydroiso-JI-lapachone, dehydro-a-lapachone, a-lapachone and Jl-lapachone by the reaction with aqueous NaN02 and glacial AcOH; adenophyllone, quadrllone and dehydro-a-lapachone by the reaction with boiUng pyridine; naphthaqulnoxallne and naphtha-azaqulnoxallne derivatives by the reaction with 1, 2-dlamlnes and dialkyltln dilapacholates by the reaction with dlal. kyltin dilsopropoxides have been accomplished. Notably the syntheses of rhlnacanthln-A, Jl-(1-hydroxyisopropanyl)-dlhydrofurano-1, 2-naphthoqulnone, dehydrolso-a-Iapachone, dehydroiso-JI-lapaehone, adenophyllone and quadrllone have been reported for tbe ftrst time from our group starting from lapachol. The synthesis of novel napbthaqulnoxallne and azaqulnoxallne derivatives from lapachol has been additional