K. Ogihara et al., PREPARATION OF NAPHTHOQUINONE DERIVATIVES FROM PLUMBAGIN AND THEIR ICHTHYOTOXICITY, Chemical and Pharmaceutical Bulletin, 45(3), 1997, pp. 437-445
Various naphthoquinone derivatives were prepared from a natural produc
t, 5-hydroxy-2-methyl-1,4-naphthoquinone (plumbagin); these were mostl
y substituted at C-3 through carbon-carbon bond formation mediated by
a metal-based oxidant such as lead tetraacetate in the presence of var
ious carboxylic acids. The halogenated compounds showed stronger ichth
yotoxicity than plumbagin, but other derivatives were less active.