Open Access
Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate
Publication type: Journal Article
Publication date: 2017-07-01
scimago Q1
wos Q1
SJR: 0.939
CiteScore: 10.0
Impact factor: 5.8
ISSN: 13196103, 22124640
General Chemistry
Abstract
The key intermediate of misoprostol, methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate was prepared from commercially available suberic acid in 40% yield over five steps. The key step involved a ZnCl 2 catalyzed Friedel-Crafts reaction between furan and 2,9-oxonanedione. Sulfuric acid catalyzed methylation of 8-(furan-2-yl)-8-oxooctanoic acid followed by sequential reduction and ZnCl 2 catalyzed Piancatelli rearrangement resulted in the formation of the key intermediate of misoprostol.
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Total citations:
7
Citations from 2024:
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(28.57%)
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GOST
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Jiang X. et al. Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate // Journal of Saudi Chemical Society. 2017. Vol. 21. No. 5. pp. 587-592.
GOST all authors (up to 50)
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Jiang X., Wang X., Huang X., Li G., Yu C. Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate // Journal of Saudi Chemical Society. 2017. Vol. 21. No. 5. pp. 587-592.
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RIS
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TY - JOUR
DO - 10.1016/j.jscs.2017.01.004
UR - https://doi.org/10.1016/j.jscs.2017.01.004
TI - Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate
T2 - Journal of Saudi Chemical Society
AU - Jiang, Xinpeng
AU - Wang, Xueyan
AU - Huang, Xing
AU - Li, Guizhou
AU - Yu, Chuanming
PY - 2017
DA - 2017/07/01
PB - King Saud University
SP - 587-592
IS - 5
VL - 21
SN - 1319-6103
SN - 2212-4640
ER -
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BibTex (up to 50 authors)
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@article{2017_Jiang,
author = {Xinpeng Jiang and Xueyan Wang and Xing Huang and Guizhou Li and Chuanming Yu},
title = {Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate},
journal = {Journal of Saudi Chemical Society},
year = {2017},
volume = {21},
publisher = {King Saud University},
month = {jul},
url = {https://doi.org/10.1016/j.jscs.2017.01.004},
number = {5},
pages = {587--592},
doi = {10.1016/j.jscs.2017.01.004}
}
Cite this
MLA
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Jiang, Xinpeng, et al. “Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate.” Journal of Saudi Chemical Society, vol. 21, no. 5, Jul. 2017, pp. 587-592. https://doi.org/10.1016/j.jscs.2017.01.004.