Stereocontrolled Synthesis of (-)-5,11-Dideoxytetrodotoxin.
Publication type: Journal Article
Publication date: 2001-05-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
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.
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45
Total citations:
45
Citations from 2025:
2
(4.44%)
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GOST
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Asai M. et al. Stereocontrolled Synthesis of (-)-5,11-Dideoxytetrodotoxin. // Tetrahedron. 2001. Vol. 57. No. 21. pp. 4543-4558.
GOST all authors (up to 50)
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Asai M., NISHIKAWA T., Ohyabu N., YAMAMOTO N., ISOBE M. Stereocontrolled Synthesis of (-)-5,11-Dideoxytetrodotoxin. // Tetrahedron. 2001. Vol. 57. No. 21. pp. 4543-4558.
Cite this
RIS
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TY - JOUR
DO - 10.1016/S0040-4020(01)00382-9
UR - https://doi.org/10.1016/S0040-4020(01)00382-9
TI - Stereocontrolled Synthesis of (-)-5,11-Dideoxytetrodotoxin.
T2 - Tetrahedron
AU - Asai, Masanori
AU - NISHIKAWA, Toshio
AU - Ohyabu, Norio
AU - YAMAMOTO, NOBORU
AU - ISOBE, Minoru
PY - 2001
DA - 2001/05/01
PB - Elsevier
SP - 4543-4558
IS - 21
VL - 57
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
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@article{2001_Asai,
author = {Masanori Asai and Toshio NISHIKAWA and Norio Ohyabu and NOBORU YAMAMOTO and Minoru ISOBE},
title = {Stereocontrolled Synthesis of (-)-5,11-Dideoxytetrodotoxin.},
journal = {Tetrahedron},
year = {2001},
volume = {57},
publisher = {Elsevier},
month = {may},
url = {https://doi.org/10.1016/S0040-4020(01)00382-9},
number = {21},
pages = {4543--4558},
doi = {10.1016/S0040-4020(01)00382-9}
}
Cite this
MLA
Copy
Asai, Masanori, et al. “Stereocontrolled Synthesis of (-)-5,11-Dideoxytetrodotoxin..” Tetrahedron, vol. 57, no. 21, May. 2001, pp. 4543-4558. https://doi.org/10.1016/S0040-4020(01)00382-9.