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
Further Information

Publication History

Publication Date:
21 February 2008 (online)

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.