The first total syntheses of the orchid-derived natural products isoarundinin I (1), (±)-bleochrin F ((±)-2), (±)-blestanol K ((±)-3), and (±)-pleionol ((±)-4) from renewable starting materials are reported, along with the evaluation of their biological activities. The total syntheses were based on regioselective aromatic bromination reactions in combination with a key acidpromoted regioselective intramolecular cyclization. The biological results suggest that isoarundinin I ( 1), (±)-blestanol K ((±)-3), and (±)-pleionol ((±)-4) have the potential to inhibit the growth of both sensitive and multidrug-resistant cancer cells.
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