Synthesis of bisenarsan; an organoarsenic metabolite from streptomycetes

Abstract

The first synthesis of bisenarsan; the (4S,6S,Z)-2,4,6-trimethylnon- 2-enoic acid ester of (2-hydroxyethyl)arsonic acid, is described. Its absolute configuration is experimentally determined by preparing both enantiomers and comparing these to the natural isolate. The synthesis comprises 10 steps and required the development of an improved, versatile (2-hydroxyethyl)arsonic acid building block. The availability of bisenarsan together with the acquired insight into organoarsenic chemistry supports studies on the unique bioactivities of arsenic-containing secondary metabolites