A Convenient Synthesis of 6-Hydroxy-7,9-bis(<i>p</i>-methoxybenzyl)-5-methylene-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione

Abstract

Abstract The title compound, the key intermediate for a total synthesis of bicyclomycin, was synthesized from N,N′-diacetyl anhydroglycine through twelve steps. The three-carbon branch for the construction of the bicyclic skeleton was introduced to the 2,5-piperazinedione ring as an alkylidene substituent, and then the olefinic function was converted into a diol function. The formation of bicyclic ring was achieved by treatment with N-bromosuccinimide followed by the intramoleculer substitution of the primary hydroxyl group in the side chain, and finally the secondary hydroxyl group was converted to the methylene function by an improved Peterson reaction.