Asymmetric Total Synthesis of Neoxaline
Publication type: Journal Article
Publication date: 2013-08-19
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
23957424
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
A first asymmetric total synthesis and determination of the absolute configuration of neoxaline has been accomplished through the highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (-)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline as the key steps.
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Metrics
45
Total citations:
45
Citations from 2024:
6
(13%)
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MLA
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GOST
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Ideguchi T. et al. Asymmetric Total Synthesis of Neoxaline // Journal of the American Chemical Society. 2013. Vol. 135. No. 34. pp. 12568-12571.
GOST all authors (up to 50)
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Ideguchi T., Yamada T., Shirahata T., Hirose T., Sugawara A., Kobayashi Y., Omura S., SUNAZUKA T. Asymmetric Total Synthesis of Neoxaline // Journal of the American Chemical Society. 2013. Vol. 135. No. 34. pp. 12568-12571.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ja406657v
UR - https://doi.org/10.1021/ja406657v
TI - Asymmetric Total Synthesis of Neoxaline
T2 - Journal of the American Chemical Society
AU - Ideguchi, Tetsuya
AU - Yamada, Takeshi
AU - Shirahata, Tatsuya
AU - Hirose, Tomoyasu
AU - Sugawara, Akihiro
AU - Kobayashi, Yoshinori
AU - Omura, Satoshi
AU - SUNAZUKA, TOSHIAKI
PY - 2013
DA - 2013/08/19
PB - American Chemical Society (ACS)
SP - 12568-12571
IS - 34
VL - 135
PMID - 23957424
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2013_Ideguchi,
author = {Tetsuya Ideguchi and Takeshi Yamada and Tatsuya Shirahata and Tomoyasu Hirose and Akihiro Sugawara and Yoshinori Kobayashi and Satoshi Omura and TOSHIAKI SUNAZUKA},
title = {Asymmetric Total Synthesis of Neoxaline},
journal = {Journal of the American Chemical Society},
year = {2013},
volume = {135},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/ja406657v},
number = {34},
pages = {12568--12571},
doi = {10.1021/ja406657v}
}
Cite this
MLA
Copy
Ideguchi, Tetsuya, et al. “Asymmetric Total Synthesis of Neoxaline.” Journal of the American Chemical Society, vol. 135, no. 34, Aug. 2013, pp. 12568-12571. https://doi.org/10.1021/ja406657v.