Synthetic studies on bicyclomycin I synthesis of 1-allyl and benzoyl-8,10-dimethyl-6-methoxy-5-methylene-8,10-diaza-2-oxabicyclo[4.2.2]Decane-7,9-dione, which have the bicyclo ring system found in antibiotic bicyclomycin

Regiospecific cyclization of the alcohol 8 into the bicyclo[ 4.2.2] compound 12 was achieved via selective activation of the secondary methoxy group and subsequent acid treatment. A side-chain was introduced at the bridge-head position, thus making up the bicyclomycin skeleton.