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Synthesis of Three Marine Natural Sesterterpenolides from Methyl Isoanticopalate. First Enantioselective Synthesis of Luffolide

2005; American Chemical Society; Volume: 70; Issue: 23 Linguagem: Inglês

10.1021/jo0515529

1520-6904

P. Basabe, Sergio Delgado, Isidro S. Marcos, David Dı́ez, A. Diego, M. De Román, Julio G. Urones,

Asymmetric Synthesis and Catalysis

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 γ-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.