Sporolides

Sporolides A and B are polycyclic macrolides extracted from the obligate marine bacterium Salinispora tropica, which is found in ocean sediment.

[1] They were the second group of compounds (after salinosporamide A) isolated from Salinispora, and were said to indicate the potential of marine actinomycetes as a source of novel secondary metabolites.

The complex aromatic structure of the sporolides was hypothesized to be derived from an unstable nine-membered ring enediyne precursor, which could undergo Bergman cyclization to generate a para-benzyne intermediate.

Nucleophilic attack by chloride would account for the 1:1 mixture of sporolide A and B and for the single chlorine in these enediyne-derived natural products.

The first total synthesis of sporolide B was reported by K. C. Nicolaou's group and used a highly stereoselective and convergent strategy that involved two cycloaddition reactions.