Download PDF
Synfacts 2009(5): 0467-0467  
DOI: 10.1055/s-0028-1088173
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Gonyautoxin 3

Contributor(s):Philip Kocienski, Indu Dager
J. V. Mulcahy, J. Du Bois*
Stanford University, USA
A Stereoselective Synthesis of (+)-Gonyautoxin 3
J. Am. Chem. Soc.  2008,  130:  12630-12631  
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
22 April 2009 (online)

 PDF Download Permissions and Reprints

Key words

gonyautoxins - amination - nitrenes - rhodium - sulfation

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.

Comment

The amination reaction (D → E) is proposed to proceed via aziridination at C4 and C12 followed by a nucleophilic attack at C10 by acetic acid which is formed as a byproduct in the reaction. GTX 3 epimerizes to GTX 2 in aqueous acidic solution.

   Permissions and Reprints