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

Toshio Nishikawa, Daisuke Urabe, Masaatsu Adachi, Minoru Isobe

研究成果: Article査読

10 被引用数 (Scopus)

抄録

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.

本文言語English
論文番号st-2015-a0167-a
ページ(範囲)1930-1939
ページ数10
ジャーナルSynlett
26
14
DOI
出版ステータスPublished - 2015 9月 1
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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