Novel and diverse mollugin analogues (1–12) were synthesized using PhB(OH) 2 /AcOH-mediated electrocyclization reaction as a key step. The newly synthesized compounds were screened for antioxidant and antibacterial activities. Compounds 1, 2, 5, 6, 8, and 10–12 showed high antioxidant activities in DPPH inhibition (IC 50 =0.52–1.11μM) compared with BHT (IC 50 =9.67μM). Compounds 3 exhibited potent antibacterial activity against Staphylococcus aureus (KCTC-1916) bacterial strain at 100μg/mL. Structures of newly synthesized compounds were confirmed by IR, 1 H NMR, 13 C NMR data and high-resolution mass spectrometry.