Stereoselective and efficient total synthesis of optically active tetrodotoxin from D-glucose.

@article{Sato2008StereoselectiveAE,
  title={Stereoselective and efficient total synthesis of optically active tetrodotoxin from D-glucose.},
  author={Ken-ichi Sato and Shoji Akai and Hirotsugu Shoji and Naoki Sugita and Shiho Yoshida and Yoshinao Nagai and Katsuhiko Suzuki and Yoshiyuki Nakamura and Yasuhiro Kajihara and Masuo Funabashi and Juji Yoshimura},
  journal={The Journal of organic chemistry},
  year={2008},
  volume={73 4},
  pages={
          1234-42
        }
}
A stereoselective and efficient total synthesis of optically active tetrodotoxin (TTX) is described. A polyfunctionalized key cyclitol compound containing branched-chains for the synthesis of TTX was prepared from D-glucose employing the Henry reaction (Nitro aldol reaction) as the key transformation. Stereoselective construction of the alpha-azido-aldehyde branched-chain was achieved via the key spiro alpha-chloroepoxide intermediate. 
BETA

Similar Papers

Figures, Tables, and Topics from this paper.

Citations

Publications citing this paper.
SHOWING 1-10 OF 11 CITATIONS

The molecular mystique of tetrodotoxin.

  • Toxicon : official journal of the International Society on Toxinology
  • 2012
VIEW 1 EXCERPT
CITES METHODS
HIGHLY INFLUENCED

References

Publications referenced by this paper.

For review of the Henry reaction see : Luzzio , F . A

K. Sato, S. Akai, +4 authors J. Yoshimura
  • J . Org . Chem .
  • 2005