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Synfacts 2006(9): 0870-0870  
DOI: 10.1055/s-2006-942053
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Saxitoxin

Contributor(s): Philip Kocienski, Fiona Black
J. J. Fleming, J. Du Bois*
Stanford University, USA
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

(+)-Saxitoxin is a paralytic agent from oceanic red tides. It blocks cationic influx through voltage-dependent Na+ channels. Notable features of the synthesis include formation of a medium-sized guanidine ring from a carbodiimide and regio- and stereoselective oxidation of alkene C to hydroxyketone D.