Stereostructure and synthetic study of dilactone macrolide luminamicin, an anaerobic antibiotic

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In the course of screening for antianaerobic antibiotics of actinomycete origin, we have found a new antibiotic, luminamicin, which showed antibacterial activity against anaerobic bacteria, especially against Clostridium sp. Its architectural feature is a decalin ring system fused to a 10-membered macrolactone which in turn is fused to a 14-membered macrolactone possessing an enol ether in conjugation with an unsaturated cyclic anhydride functionality, and this compound has 11 asymmetric centers.The absolute stereostructure of luminamicin, an anaerobic antibiotic, has been determined by using conformational analysis via high-temperature molecular dynamics, NMR spectroscopy, and the modified Mosher method. We also have synthesized this molecule. We divide the three parts (northern part, middle part, and southern part). 3,4-Disubstituted furan has constructed from 4-phenyloxazole and alkynal via Diels-Alder Retro-Diels-Alder reaction. And middle part has constructed via Frdter's alkylation with BOMC1 and Reformatsky reaction. And also, the construction of oxa-bridge have formed by intramolecular Michael addition and intermolecular Aldol reaction.