Stereocontrolled synthesis of (−)-5,11-dideoxytetrodotoxin

Asymmetric synthesis of (−)-5,11-dideoxytetrodotoxin, an analog of puffer fish toxin, was accomplished from a common key intermediate through a novel hydroxylation at the C-8 position with neighboring group participation of trichloroacetamide, a highly stereoselective addition of acetylide as an equ...

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Bibliographic Details
Published inTetrahedron Vol. 57; no. 21; pp. 4543 - 4558
Main Authors Asai, Masanori, Nishikawa, Toshio, Ohyabu, Norio, Yamamoto, Noboru, Isobe, Minoru
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 21.05.2001
Elsevier
Subjects
asymmetric synthesis
Chemistry
Chemistry, Organic
guanidine
marine metabolites
Physical Sciences
Science & Technology
tetrodotoxin
guanidine
asymmetric synthesis
tetrodotoxin
marine metabolites
TRICHLOROACETAMIDE
INTERMEDIATES POTENTIALLY USEFUL
(-)-TETRODOTOXIN
HYDROXY
ANALOGS
TARICHA-GRANULOSA
SUGARS
DERIVATIVES
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Summary:Asymmetric synthesis of (−)-5,11-dideoxytetrodotoxin, an analog of puffer fish toxin, was accomplished from a common key intermediate through a novel hydroxylation at the C-8 position with neighboring group participation of trichloroacetamide, a highly stereoselective addition of acetylide as an equivalent of carboxylic acid, and a new guanidine synthesis from trichloroacetamide as key steps. This study presents the first asymmetric synthesis among tetrodotoxin and its analogs. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00382-9