The objective of the proposed research is the total synthesis of the novel antibiotic bicyclomycin in optically active form and of select bicyclomycin analogs to be used in evaluating the chemical mechanism of antibacterial action of bicyclomycin. New synthetic methods for constructing the bicyclomycin ring system will be investigated. The synthetic strategem is of sufficient bravity and versatility to allow the elaboration of bicyclomycin and all synthetic analogs from a few common intermediates. By these methods, the chemical structural and dynamic properties of the bicyclomycin ring system as a "latent" Alpha,Beta-unsaturated pryuvamide (Michael acceptor) will be investigated.