ORGN 244 |
| In 1992 Vidal and co-workers reported the isolation and biological activities of lituarines A-C (1-3), architecturally complex marine natural products isolated from the sea pen Lituaria australasaie, endemic to the western region of the New Caledonian Lagoon near the Baie de St. Vincent. The structures of the lituarines, including the connectivities and relative stereochemistries, were based solely on multi-dimensional NMR techniques. From the biomedical perspective, the lituarines display significant cytotoxicities toward KB cells [(1): IC50 = 5.5 - 7.5 nM; (2): IC50 = 1-3 nM; (3): IC50 = 7-9 nM]. Intrigued both by the architecture and the biological activities of the lituarines we initiated a research program directed toward a unified total synthesis of the lituarines. We recently completed the syntheses of the structures assigned to lituarines B and C; unfortunately the spectral properties did not match those reported for the natural lituarines. The total syntheses of the assigned structures of lituarines B and C, as well as possible structural revision of the lituarines, will be presented.
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H. C. Brown Legacy Symposium
8:30 AM-12:00 PM, Monday, 11 September 2006 Moscone Center -- Room 134, Oral
Division of Organic Chemistry |
