Synthesis of an esperamicin core analog with an epoxide trigger

Article abstract of DOI:10.1016/S0040-4039(96)02009-6

An esperamicin core analog 4 with an epoxide trigger like that found in the related enediyne, dynemicin, was prepared. Surprisingly, it was found to be relatively stable; the p-aminophenyl substituent did not facilitate epoxide solvolysis to the extent that had been anticipated. A mild acid, pyridinium p-toluenesulfonate, was found to induce solvolysis of 4 and led to the formation of the cycloaromatized product 25.