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Synfacts 2008(3): 0233-0233  
DOI: 10.1055/s-2008-1042654
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Decarbamoyloxysaxitoxin

Contributor(s): Philip Kocienski
O. Iwamoto, H. Koshino, D. Hashizume, K. Nagasawa*
Tokyo University of Agriculture and Technology and RIKEN, Wako, Japan
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Publikationsdatum:
21. Februar 2008 (online)

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Significance

(-)-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.