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Synfacts 2009(5): 0467-0467
DOI: 10.1055/s-0028-1088173
DOI: 10.1055/s-0028-1088173
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (+)-Gonyautoxin 3
J. V. Mulcahy, J. Du Bois*
Stanford University, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. April 2009 (online)
Significance
Gonyautoxin, saxitoxin and neosaxitoxin are the major constituents of paralytic shellfish poisons. They inhibit electrical conduction in cells by acting as a stopper in ion flux through voltage-gated Na+ channels. The first asymmetric synthesis of gonyautoxin 3 (GTX 3) features a rhodium-catalyzed amination reaction (D → E) to access the tricyclic core of the toxin which is found in more than thirty natural products.