Toward the total synthesis of a hybrid natural product that consists a highly functionalized 11-oxatricycloundecane/macrolide and its structure activity relationships

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Luminamicin (1) was found to exhibit selective antibacterial activity against anaerobic bacteria in 1985. It contains a highly functionalized 11-oxatricycloundecane, associated with a 10-membered lactone moiety which possesses a (E)-trisubstituted olefin and a 14-membered macrolactone, with an enol ether conjugated with a maleic anhydride functionality.We have been focusing on its total synthesis due to its intriguing structure and interesting biological activity. We synthesized a framework of the key intermediate from the unsaturated aldehyde via intramolecular 1,6-oxa-Michael reaction and stereoselective protonation at C4 position. Study toward the total synthesis of 1 is in progress in our laboratory.