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Synthesis of (-)-Decarbamoyloxysaxitoxin
O. Iwamoto, H. Koshino, D. Hashizume, K. Nagasawa*
Tokyo University of Agriculture and Technology and RIKEN, Wako, Japan
21 February 2008 (online)
(-)-Decarbamoyloxysaxitoxin is a metabolite of the Australian shellfish Gymnodinium catenatum. The synthesis features a 1,3-dipolar cycloaddition to establish three contiguous stereogenic centers in B and a novel α-hydroxylation of the ketone E using IBX.