Multifunctionality of the N -Trichloroacetyl Group Developed in the Synthesis of Tetrodotoxin, a Puffer Fish Toxin

Toshio Nishikawa, Daisuke Urabe, Masaatsu Adachi, Minoru Isobe

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)


This account describes a serendipitous discovery and the development of unique reactions associated with trichloroacetamide during synthetic studies of tetrodotoxin in our laboratory. The reactions include site-selective hydroxylation using the neighboring-group participation of trichloroacetamide, guanidinylation from a trichloroacetamide, protecting-group transformation, and removal of the N-trichloroacetyl group. These studies indicate the importance of the total synthesis of densely functionalized natural products as a field for the development of new reactions. 1 Introduction 2 Improvement of the Conditions for the Overman Rearrangement to Introduce Trichloroacetamide 3 Site-Selective Hydroxylation Using the Neighboring-Group Participation of Trichloroacetamide 4 Guanidine Synthesis 5 Protecting-Group Transformation of the N-Trichloroacetyl Group 6 New Deprotection Conditions for the Removal of the N-Trichloroacetyl Group 7 Conclusion.

Original languageEnglish
Article numberst-2015-a0167-a
Pages (from-to)1930-1939
Number of pages10
Issue number14
Publication statusPublished - 2015 Sept 1


  • neighboring-group effects
  • protecting groups
  • protecting-group transformations
  • tetrodotoxin
  • trichloroacetamide


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