Lupalbigenin () is an antibacterial isoflavone isolated from (Lour.) Corner (Moraceae). In this study, we achieved the first gram-scale synthesis of lupalbigenin () from commercially available genistein (), with a yield of 47.7%. The key step was a Claisen rearrangement that simultaneously installed two prenyl groups at the C-6 and C-11 positions of lupalbigenin (). Antimicrobial activity assays revealed that lupalbigenin () exhibited rapid bactericidal activity, inhibited α-hemolysin and biofilm formation, and disrupted bacterial cell membranes. These findings suggest that lupalbigenin () is a promising candidate for the development of novel antibiotics to combat bacterial infections.
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