Development of approaches to fibrostatin F, N-acetyl-L-cysteinyl-containing 1,4-naphthoquinone metabolite of Streptomyces catenulae

Abstract

A possibility of the synthesis of microbial metabolite Streptomyces catenulae fibrostatin F through the AcOH-catalyzed condensation of 5-hydroxy-3-hydroxymethyl-2,7-dimethoxy1,4-naphthoquinone and its related 3-chloromethyl, 3-acetoxymethyl, and 3-methoxymethyl derivatives with N-acetyl-L-cysteine and paraformaldehyde in 1,4-dioxane was studied. In these conditions, all naphthoquinones gave N-acetyl-S-[(8-hydroxy-3,6-dimethoxy-1,4-dioxonaphthalen-2-yl)methyl]-L-cysteine isomeric to the natural fibrostatin C.