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

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

Content Provider	Scilit
Author	Nishikawa, Toshio Isobe, Minoru Urabe, Daisuke Adachi, Masaatsu
Copyright Year	2015
Description	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
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0034-1380781.pdf
Ending Page	1939
Page Count	10
Starting Page	1930
ISSN	09365214
e-ISSN	14372096
DOI	10.1055/s-0034-1380781
Journal	Synlett
Issue Number	14
Volume Number	26
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2015-07-24
Access Restriction	Open
Subject Keyword	Organic Chemistry Protecting Groups Trichloroacetamide Neighboring-group Effects Protecting-group Transformations
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry

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