A Synthesis of (+)-Saxitoxin
Publication type: Journal Article
Publication date: 2006-03-01
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
16551097
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
An asymmetric synthesis of the bis-guanidinium poison, (+)-saxitoxin (STX), is described. Commencing from an N,O-acetal starting material made readily available through sulfamate ester C-H amination, the completed route to STX showcases the utility of oxathiazinane dioxide heterocycles for the assembly of polyfunctionalized amine derivatives. In the final preparative stages, an unusual nine-membered ring guanidine intermediate is oxidized selectively and made to undergo dehydrative cyclization to afford the tricyclic core of the natural product. Access to STX and related structures will provide unique pharmacological tools for the study of voltage-regulated Na+ ion channel proteins.
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218
Total citations:
218
Citations from 2025:
6
(2.75%)
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MLA
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GOST
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Fleming J. J., Du Bois J. S. A Synthesis of (+)-Saxitoxin // Journal of the American Chemical Society. 2006. Vol. 128. No. 12. pp. 3926-3927.
GOST all authors (up to 50)
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Fleming J. J., Du Bois J. S. A Synthesis of (+)-Saxitoxin // Journal of the American Chemical Society. 2006. Vol. 128. No. 12. pp. 3926-3927.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ja0608545
UR - https://doi.org/10.1021/ja0608545
TI - A Synthesis of (+)-Saxitoxin
T2 - Journal of the American Chemical Society
AU - Fleming, James J
AU - Du Bois, Jon S.
PY - 2006
DA - 2006/03/01
PB - American Chemical Society (ACS)
SP - 3926-3927
IS - 12
VL - 128
PMID - 16551097
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
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@article{2006_Fleming,
author = {James J Fleming and Jon S. Du Bois},
title = {A Synthesis of (+)-Saxitoxin},
journal = {Journal of the American Chemical Society},
year = {2006},
volume = {128},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/ja0608545},
number = {12},
pages = {3926--3927},
doi = {10.1021/ja0608545}
}
Cite this
MLA
Copy
Fleming, James J., and Jon S. Du Bois. “A Synthesis of (+)-Saxitoxin.” Journal of the American Chemical Society, vol. 128, no. 12, Mar. 2006, pp. 3926-3927. https://doi.org/10.1021/ja0608545.