Asymmetric Total Synthesis of Fusarentin 6-Methyl Ether and Its Biomimetic Transformation into Fusarentin 6,7-Dimethyl Ether, 7-O-Demethylmonocerin, and (+)-Monocerin
Bowen Fang
1
,
Xingang Xie
1
,
Changgui Zhao
1
,
Peng Jing
1
,
Huilin Li
1
,
Zhengshen Wang
1
,
Jixiang Gu
1
,
Xuegong She
1, 2
Publication type: Journal Article
Publication date: 2013-06-07
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
23713975
Organic Chemistry
Abstract
A concise asymmetric total synthesis of a fusarentin ether (1) with sequential biomimetic transformation to its analogues fusarentin 6,7-dimethyl ether (2), 7-O-demethylmonocerin (3), and (+)-monocerin (4) has been accomplished. The cis-fused furobenzopyranones of 7-O-demethylmonocerin (3) and (+)-monocerin (4) were efficiently constructed via an intramolecular nucleophilic trapping of a quinonemethide intermediate, which was obtained by benzylic oxidation of fusarentin 6-methyl ether (1) using hypervalent iodine reagent.
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34
Total citations:
34
Citations from 2024:
3
(8.82%)
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GOST
Copy
Fang B. et al. Asymmetric Total Synthesis of Fusarentin 6-Methyl Ether and Its Biomimetic Transformation into Fusarentin 6,7-Dimethyl Ether, 7-O-Demethylmonocerin, and (+)-Monocerin // Journal of Organic Chemistry. 2013. Vol. 78. No. 12. pp. 6338-6343.
GOST all authors (up to 50)
Copy
Fang B., Xie X., Zhao C., Jing P., Li H., Wang Z., Gu J., She X. Asymmetric Total Synthesis of Fusarentin 6-Methyl Ether and Its Biomimetic Transformation into Fusarentin 6,7-Dimethyl Ether, 7-O-Demethylmonocerin, and (+)-Monocerin // Journal of Organic Chemistry. 2013. Vol. 78. No. 12. pp. 6338-6343.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo400760q
UR - https://doi.org/10.1021/jo400760q
TI - Asymmetric Total Synthesis of Fusarentin 6-Methyl Ether and Its Biomimetic Transformation into Fusarentin 6,7-Dimethyl Ether, 7-O-Demethylmonocerin, and (+)-Monocerin
T2 - Journal of Organic Chemistry
AU - Fang, Bowen
AU - Xie, Xingang
AU - Zhao, Changgui
AU - Jing, Peng
AU - Li, Huilin
AU - Wang, Zhengshen
AU - Gu, Jixiang
AU - She, Xuegong
PY - 2013
DA - 2013/06/07
PB - American Chemical Society (ACS)
SP - 6338-6343
IS - 12
VL - 78
PMID - 23713975
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2013_Fang,
author = {Bowen Fang and Xingang Xie and Changgui Zhao and Peng Jing and Huilin Li and Zhengshen Wang and Jixiang Gu and Xuegong She},
title = {Asymmetric Total Synthesis of Fusarentin 6-Methyl Ether and Its Biomimetic Transformation into Fusarentin 6,7-Dimethyl Ether, 7-O-Demethylmonocerin, and (+)-Monocerin},
journal = {Journal of Organic Chemistry},
year = {2013},
volume = {78},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/jo400760q},
number = {12},
pages = {6338--6343},
doi = {10.1021/jo400760q}
}
Cite this
MLA
Copy
Fang, Bowen, et al. “Asymmetric Total Synthesis of Fusarentin 6-Methyl Ether and Its Biomimetic Transformation into Fusarentin 6,7-Dimethyl Ether, 7-O-Demethylmonocerin, and (+)-Monocerin.” Journal of Organic Chemistry, vol. 78, no. 12, Jun. 2013, pp. 6338-6343. https://doi.org/10.1021/jo400760q.