ORGN 33 |
| Gymnodimine is a marine biotoxin isolated in 1995 by Yasumoto and coworkers from New Zealand oysters Tiostrea chilensis and is produced by the dinoflagellate Gymnodiminium cf. mikimotoi, a single-celled algae responsible for red tides due to massive multiplication. The toxin has been implicated in several incidents of neurotoxic shellfish and human poisoning (LD50 = 96 µg/kg in a mouse bioassay). The unique structural features which include a 6,6-spirocyclic imine ring system (proposed pharmacophore), a trisubstituted tetrahydrofuran segment embedded within a 16-membered ring carbocycle, and a butenolide moiety, coupled with the potentially novel mechanism of action prompted us to develop a synthetic strategy toward the total synthesis of the natural product. Having achieved the preparation of the tetrahydrofuran and spirolactam fragments, we turned our focus to the coupling of the two key fragments and annulation of the chiral butenolide group. This presentation will describe studies and further progress toward gymnodimine, with emphasis on construction of the butenolide.
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Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- 202B, Oral
Division of Organic Chemistry |
