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Synfacts 2019; 15(02): 0109
DOI: 10.1055/s-0037-1611971
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Saxitoxin and 11-Saxitoxinethanoic Acid

Contributor(s):
Erick M. Carreira
,
Felix Pultar
Walker JR, Merit JE, Thomas-Tran R, Tang DT. Y, Du Bois J. * Stanford University, USA
Divergent Synthesis of Natural Derivatives of (+)-Saxitoxin Including 11-Saxitoxinethanoic Acid.

Angew. Chem. Int. Ed. 2019;
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Further Information

Publication History

Publication Date:
18 January 2019 (online)

 
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Key words

(+)-saxitoxin - saxitoxinethanoic acid - Evans–Mislow rearrangement - Liebeskind–Stille–Migita coupling

Significance

The authors report the total syntheses of (+)-saxitoxin and several structural analogues including saxitoxinethanoic acid. These bis-guanidinium natural products have been of high interest due to their extraordinary activity against voltage-gated sodium ion channels.


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Comment

Electrophilic aromatic substitution and rhodium-catalyzed oxidative cyclization yield tricyclic system E from simple starting materials. Clever application of an Evans–Mislow rearrangement gives access to advanced intermediate F that is used to complete the synthesis of both target structures.


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