Synthesis of three marine natural sesterterpenolides from methyl isoanticopalate. First enantioselective synthesis of luffolide.

The Journal of organic chemistry

PubMedID: 16268623

Basabe P, Delgado S, Marcos IS, Diez D, Diego A, de Román M, Urones JG. Synthesis of three marine natural sesterterpenolides from methyl isoanticopalate. First enantioselective synthesis of luffolide. J Org Chem. 2005;70(23):9480-5.
[Reaction: see text]. The synthesis of three marine sponge metabolites, luffolide (4), 5, and 6, are described for the first time, establishing the absolute configuration of these compounds. The key intermediate, aldehyde 17, was obtained from methyl isoanticopalate, 11. The addition of 3-furyllithium to 17 and subsequent photochemical oxidation give the gamma-hydroxybutenolide 5 and its epimer at C-16. Sesterterpenolide 6 is obtained by dehydration of 5. From the key aldehyde 17, luffolide (4) was obtained in six steps.