Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
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A New Synthetic Route to the Skeleton of Saxitoxin, a Naturally Occurring Blocker of Voltage-Gated Sodium Channels
Yusuke SawayamaToshio Nishikawa
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2012 Volume 70 Issue 11 Pages 1178-1186

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Abstract

Saxitoxin is as potent and specific blocker of voltage-gated sodium channels as tetrodotoxin. This unique biological activity has established the importance of these two small natural products in neurophysiological experiments. In order to find new blockers of the voltage-gated sodium channels, an efficient synthetic route to the skeleton of saxitoxin was developed. This new synthetic route is based on two key reactions (i) cascade cyclization of a guanidino-acetylene initiated by the bromocation (Br+) and (ii) transformation of the geminal-dibromomethylene moiety to enol acetate, and culminated in the total synthesis of decarbamoyl-α-saxitoxinol, a naturally-occurring analog of saxitoxin.

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© 2012 The Society of Synthetic Organic Chemistry, Japan
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