Approaches to the synthesis of bicyclomycin

Abstract

3-Acetoxy-1, 4-dibenzyl-3-(3-methoxy-1-methyl-enepropyl)piperazine-2, 5-dione (4) has been synthesized both via cyclization of N-benzyl-N(N-benzylcarbamoylmethyl)-5-methoxy-3-methylene-2-oxopentanamide (10) and via cleavage of the epoxide ring of 4, 7-dibenzyl-2-(2-methoxyethyl)-2-methyl-1-oxa-4, 7-diazaspiro [2.5]-octane-5, 8-dione (12); the hydroxy-compound (2) corresponding to (4) has been synthesized via cyclization of the (tetrahydropyran-2-yloxy)ethyl compound (15) corresponding to (10).