Synthesis of lepiochlorin, a chlorinated antibiotic, by use of electrochemical haloalkoxylation

Article abstract of DOI:10.1246/bcsj.56.2183

Lepiochlorin is an antibiotic butenolide, a chlorinated metabolite of a fungus cultivated by a leaf-cutting ant. It was synthesized from 2-methyl-4-oxopentanoic acid by the electrochemical chloromethoxylation of 2-methyl-2,4-pentadien-4-olide in the MeOH-NH//4Cl-(Pt-Pt) system followed by hydrolysis in a mixed solution of dioxane-H//2O-concd HCl (25/10/1 V/V/V) in 38% overall yield. 14 reefs.