Biologically Active Substances by Use of Electrochemical Oxidation Associate Professor

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Anodic oxidation of lactoms was very useful for the synthetic organic chemistry. We have already reported the new synthetic method of 4-acetoxy-2-azatidinones from 4-carboxy-2-azetidinones by use of electrochemical oxidation. Namely, 4-carboxy-2-azatidinone was electrolyzed in an undivided cell using platinum plates as electrode in the presence of AcONa as electrolyte in AcOH-CH_3CN to give 4-acetoxy-2-azetidinone in high yield. Using this method, a new synthetic method of optically active 3-hydroxy-ethyl-4-acetoxy-2-azetidinone which was an intermediate for the synthesis of thienamycin and its analogues, was developed and a formal total synthesis of (+)-PS-5 was achieved. This method was applied for the synthesis of gamma-lactams. Pyroglutamic acid was electrolyzed to afford 2-acetoxy-pyrrolldone in good yield. In a similar manner, compounds2a and 2b were obtained from 1a and 1b. Subsequently, C-C bond formation at 2-position of pyrrolldone was tried. Compound 6__- which was obtained by electrolysis from compound 5__- was treated with TiCl_4 to provide indollzidine derivative in good yield. Thus, the new method for the synthesis of bicyclic lactams by electrolysis from lactams having carboxy group at alpha-position of nitrogen was developed.