Total Synthesis of Bacillariolide III

Bacillariolide III was isolated from the culture medium of the marine diatom, Pseudonitzschia multi series, a causative organism of amnesic shellfish poisoning by Shimizu et al. This extracellular metabolite features bicyclic system of hydroxycyclopentane and (Z)-pentenoic acid-bearing lactone ring. Bacillariolide I is known to possess significant inhibitory activity against phospholipase A$_2$, but the biological function of bacillariolide III is still under investigation. The unique structural feature as well as the promising biological activity led us to the total synthesis of bacillariolide III. (omitted)