Journal of Organic Chemistry 2013-02-15

An improved synthesis of (-)-5,11-dideoxytetrodotoxin.

Masaatsu Adachi, Takuya Imazu, Minoru Isobe, Toshio Nishikawa

Index: J. Org. Chem. 78(4) , 1699-705, (2013)

Full Text: HTML

Abstract

We describe an improved synthesis of (-)-5,11-dideoxytetrodotoxin from an enone, which was used for synthesis of tetrodotoxin and its analogues in this laboratory. One of the major modifications was to establish a two-step guanidinylation of trichloroacetamide of a highly functionalized intermediate, which allowed us to prepare (15)N(2)-labeled 5,11-dideoxytetrodotoxin for biosynthetic investigations.

Related Compounds

  • Guanidine hydrochl...
  • 2,2,2-Trichloroace...
  • Guanidine sulfate

Related Articles:

A vaccine formulation combining rhoptry proteins NcROP40 and NcROP2 improves pup survival in a pregnant mouse model of neosporosis.

2015-01-30

[Vet. Parasitol. 207(3-4) , 203-15, (2015)]

Serum- and growth-factor-free three-dimensional culture system supports cartilage tissue formation by promoting collagen synthesis via Sox9-Col2a1 interaction.

2014-08-01

[Tissue Eng. Part A 20(15-16) , 2224-33, (2014)]

Affinity precipitation of a monoclonal antibody from an industrial harvest feedstock using an ELP-Z stimuli responsive biopolymer.

2014-08-01

[Biotechnol. Bioeng. 111(8) , 1595-603, (2014)]

Spironolactone and dimethylsulfoxide effect on glucose metabolism and oxidative stress markers in polycystic ovarian syndrome rat model.

2014-03-01

[Exp. Clin. Endocrinol. Diabetes 122(3) , 154-62, (2014)]

Injectable microcarriers as human mesenchymal stem cell support and their application for cartilage and degenerated intervertebral disc repair.

2015-01-01

[Eur. Cell. Mater. 29 , 70-80; discujssion 80-1, (2015)]

More Articles...