Synthesis of an esperamicin C (cas 107453-55-4)ore analog with an epoxide trigger

Add time:08/16/2019    Source:sciencedirect.com

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.

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