Herein, we report antibacterial and antifungal evaluation of a series of previously prepared (+)-tanikolide analogues. One analogue, (4,6)-4-methyltanikolide, displayed promising anti-methicillin-resistant activity with a MIC of 12.5 µg/mL. Based on the antimicrobial properties of the structurally related (-)-malyngolide, two further analogues (4,6)-4-methylmalyngolide and (4,6)-4-methylmalyngolide bearing a shortened -nonyl alkyl side chain were prepared in the present study using a ZrCl-catalysed deprotection/cyclisation as the key step in their asymmetric synthesis. When these were tested for activity against anti-methicillin-resistant , the MIC increased to 50 µg/mL.