Toward the Total Synthesis of Luminamicin, a Specific Anti-Anaerobic Bacteriacide

Luminamicin ( 1 ) was found to exhibit selective antibacterial activity against anaerobic bacteria by our group in 1985. It contains a highly functionalized 11-oxatricyclo[5.3.1. 1,7 0 3,8 ]undecane, associated with a 10-membered macrolactone moiety which possesses a ( E )-trisubstituted olefin and a 14-membered macrolactone, with an enol ether conjugated with a maleic anhydride functionality. Due to its intriguing structure and interesting biological activity, we have been focusing on its total synthesis. We synthesized the key intermediate ( 2 ) from the vinyltin ( 4 ) via hydrostannylation/Stille reaction and the framework of 3 from the unsaturated aldehyde ( 5 ) via intramolecular 1,6-oxa-Michael reaction. In this meeting, progress toward the total synthesis of 1 will be presented in detail.