Approaches to Construction of the Medium-Sized Ring Structure in Zetekitoxin AB by Ring-Closing Metathesis
Hayate Ishizuka
1
,
Ayato Nureki
1
,
Kanna Adachi
1
,
Yuka Takayanagi
1
,
Minami Odagi
1
,
Mari Yotsu-Yamashita
2
,
Publication type: Journal Article
Publication date: 2023-06-28
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
37378952
Organic Chemistry
Abstract
Zetekitoxin AB (ZTX), a member of the saxitoxin (STX) family isolated from the Panamanian golden frog Atelopus zeteki, shows extremely potent NaV-inhibitory activity. Here, we investigate the synthesis of 12-membered ring structure with the C11 tertiary hydroxyl group in ZTX by means of the Mislow-Evans rearrangement reaction and subsequent ring-closing metathesis reaction. Although this approach did not provide access to the 12-membered macrocycle, we obtained a new STX analog with an 18-membered macrolactam structure as a synthetic mimic of ZTX.
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Total citations:
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Citations from 2024:
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Ishizuka H. et al. Approaches to Construction of the Medium-Sized Ring Structure in Zetekitoxin AB by Ring-Closing Metathesis // Journal of Organic Chemistry. 2023. Vol. 88. No. 14. pp. 10223-10231.
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Ishizuka H., Nureki A., Adachi K., Takayanagi Y., Odagi M., Yotsu-Yamashita M., Nagasawa K. Approaches to Construction of the Medium-Sized Ring Structure in Zetekitoxin AB by Ring-Closing Metathesis // Journal of Organic Chemistry. 2023. Vol. 88. No. 14. pp. 10223-10231.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.3c00580
UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c00580
TI - Approaches to Construction of the Medium-Sized Ring Structure in Zetekitoxin AB by Ring-Closing Metathesis
T2 - Journal of Organic Chemistry
AU - Ishizuka, Hayate
AU - Nureki, Ayato
AU - Adachi, Kanna
AU - Takayanagi, Yuka
AU - Odagi, Minami
AU - Yotsu-Yamashita, Mari
AU - Nagasawa, K.
PY - 2023
DA - 2023/06/28
PB - American Chemical Society (ACS)
SP - 10223-10231
IS - 14
VL - 88
PMID - 37378952
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2023_Ishizuka,
author = {Hayate Ishizuka and Ayato Nureki and Kanna Adachi and Yuka Takayanagi and Minami Odagi and Mari Yotsu-Yamashita and K. Nagasawa},
title = {Approaches to Construction of the Medium-Sized Ring Structure in Zetekitoxin AB by Ring-Closing Metathesis},
journal = {Journal of Organic Chemistry},
year = {2023},
volume = {88},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.3c00580},
number = {14},
pages = {10223--10231},
doi = {10.1021/acs.joc.3c00580}
}
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MLA
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Ishizuka, Hayate, et al. “Approaches to Construction of the Medium-Sized Ring Structure in Zetekitoxin AB by Ring-Closing Metathesis.” Journal of Organic Chemistry, vol. 88, no. 14, Jun. 2023, pp. 10223-10231. https://pubs.acs.org/doi/10.1021/acs.joc.3c00580.
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