A New Synthetic Route to the Skeleton of Saxitoxin, a Naturally Occurring Blocker of Voltage-Gated Sodium Channels

@article{Sawayama2012ANS,
  title={A New Synthetic Route to the Skeleton of Saxitoxin, a Naturally Occurring Blocker of Voltage-Gated Sodium Channels},
  author={Yusuke Sawayama and Toshio Nishikawa},
  journal={Journal of Synthetic Organic Chemistry Japan},
  year={2012},
  volume={70},
  pages={1178-1186}
}
13 Citations
Chemical and Biological Tools for the Study of Voltage-Gated Sodium Channels in Electrogenesis and Nociception.
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To better understand the role of NaV regulation, localization, and trafficking in electrogenesis and pain pathogenesis, a number of chemical and biological reagents for interrogating NaV function have been advanced.
Biocatalytic Detoxification of Paralytic Shellfish Toxins
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The unique detoxification effect of sulfotransferases in PST biosynthesis is demonstrated, providing a potential mechanism for the development of more attractive PST-derived therapeutic analogs.
Synthesis of Dibromo Compounds Containing 2,6-Dioxabicyclo[3.1.1]heptane Similar to Core Moiety of Thromboxane A2
Thromboxane A2, a potent platelet aggregation factor, contains a labile 2,6-dioxabicyclo[3.1.1]heptane as the core moiety. Dibromo compounds with a similar core structure were synthesized by the
A Synthetic Strategy for Saxitoxin Skeleton by a Cascade Bromocyclization: Total Synthesis of (+)-Decarbamoyl-α-saxitoxinol.
TLDR
A new synthetic strategy for the formation of the ABC tricyclic framework of saxitoxin was developed, which enables the concise stereocontrolled total synthesis of (+)-decarbamoyl-α-saxitoxinol, which is a naturally occurring saxit toxin analogue.
Asymmetric synthesis of crambescin A-C carboxylic acids and their inhibitory activity on voltage-gated sodium channels.
TLDR
Structural-activity relationship studies against voltage-gated sodium channel (VGSC) inhibition using those synthetic compounds revealed that the natural enantiomer of crambescin B carboxylic acid was most active and comparable to tetrodotoxin, and the unalkylated cyclic guanidinium structure is indispensible, while the carboxylate moiety is not important.
Unexpected metal-free transformation of gem-Dibromomethylenes to ketones under acetylation conditions.
TLDR
Novel conditions for the transformation of gem-dibromomethylenes to ketones are described and a radical mechanism is proposed based on experimental results.
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