American Chemical Society
ja078293k_si_006.pdf (37.43 MB)

Total Syntheses of the Assigned Structures of Lituarines B and C

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journal contribution
posted on 2008-01-16, 00:00 authored by Amos B. Smith, Matthew O. Duffey, Kallol Basu, Shawn P. Walsh, Hans W. Suennemann, Michael Frohn
The first syntheses of the structures assigned to the marine natural products lituarines B and C have been achieved via a highly convergent sequence. The structures comprise complex, highly oxygenated 25-membered macrolactones possessing a rare tricyclic spiroketal and a unique (E,Z)-dienamide side chain. Unfortunately, the spectral properties of the synthetic compounds did not match those reported for the natural lituarines. The total syntheses of the assigned structures of lituarines B and C, as well as evidence supporting the structural assignments, are presented in this communication.