Bromocyclization of AlkynylGuanidine: A New Approach to the Synthesis of Cyclic Guanidinesof Saxitoxin

@article{Sawayama2011BromocyclizationOA,
  title={Bromocyclization of AlkynylGuanidine: A New Approach to the Synthesis of Cyclic Guanidinesof Saxitoxin},
  author={Yusuke Sawayama and Toshio Nishikawa},
  journal={Synlett},
  year={2011},
  volume={2011},
  pages={651-654}
}
Bromocyclization of propargyl and homopropargyl guanidines possessing homopropargyl alcohol provides five- and six-membered cyclic guanidines with spiro-hemiaminal, respectively, a candidate of precursors for saxitoxin. 
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5 Citations

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Citation Type

Halocyclization of Unsaturated Guanidines Mediated by Koser's Reagent and Lithium Halides.
TLDR
The synthesis of halogenated cyclic guanidines through iodine(III)-mediated umpolung of halide salts is described and their regioselectivities are described.
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.
Synthesis of Saxitoxin and Its Derivatives.
TLDR
Two consecutive carbon-nitrogen bonds at C-5 and C-6 in saxitoxin were effectively installed by the sequential Overman rearrangement of an allylic vicinal diol derived from d-malic acid.
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…
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