Open Access
Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles
Shaoren Yuan
1
,
Gabriel Guerra Faura
1
,
Hailey E Areheart
1
,
Natalie E Peulen
1
,
Stefan France
1, 2
2
Petit Institute for Bioengineering and Bioscience, Atlanta, GA 30332, USA
|
Publication type: Journal Article
Publication date: 2022-11-30
PubMed ID:
36500437
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
The development of a Lewis acid-catalyzed, intramolecular ring-opening benzannulation of 5-(indolyl)2,3-dihydrofuran acetals is described. The resulting 1-hydroxycarbazole-2-carboxylates are formed in up to 90% yield in 1 h. The dihydrofuran acetals are readily accessed from the reactions of enol ethers and α-diazo-β-indolyl-β-ketoesters. To highlight the method’s synthetic utility, a formal total synthesis of murrayafoline A, a bioactive carbazole-containing natural product, was undertaken.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
|
|
|
Journal of the American Chemical Society
1 publication, 16.67%
|
|
|
RSC Advances
1 publication, 16.67%
|
|
|
Coordination Chemistry Reviews
1 publication, 16.67%
|
|
|
Molecules
1 publication, 16.67%
|
|
|
Advanced Synthesis and Catalysis
1 publication, 16.67%
|
|
|
Russian Chemical Reviews
1 publication, 16.67%
|
|
|
1
|
Publishers
|
1
|
|
|
American Chemical Society (ACS)
1 publication, 16.67%
|
|
|
Royal Society of Chemistry (RSC)
1 publication, 16.67%
|
|
|
Elsevier
1 publication, 16.67%
|
|
|
MDPI
1 publication, 16.67%
|
|
|
Wiley
1 publication, 16.67%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 16.67%
|
|
|
1
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
6
Total citations:
6
Citations from 2024:
4
(66.66%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Yuan S. et al. Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles // Molecules. 2022. Vol. 27. No. 23. p. 8344.
GOST all authors (up to 50)
Copy
Yuan S., Guerra Faura G., Areheart H. E., Peulen N. E., France S. Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles // Molecules. 2022. Vol. 27. No. 23. p. 8344.
Cite this
RIS
Copy
TY - JOUR
DO - 10.3390/molecules27238344
UR - https://doi.org/10.3390/molecules27238344
TI - Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles
T2 - Molecules
AU - Yuan, Shaoren
AU - Guerra Faura, Gabriel
AU - Areheart, Hailey E
AU - Peulen, Natalie E
AU - France, Stefan
PY - 2022
DA - 2022/11/30
PB - MDPI
SP - 8344
IS - 23
VL - 27
PMID - 36500437
SN - 1420-3049
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2022_Yuan,
author = {Shaoren Yuan and Gabriel Guerra Faura and Hailey E Areheart and Natalie E Peulen and Stefan France},
title = {Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles},
journal = {Molecules},
year = {2022},
volume = {27},
publisher = {MDPI},
month = {nov},
url = {https://doi.org/10.3390/molecules27238344},
number = {23},
pages = {8344},
doi = {10.3390/molecules27238344}
}
Cite this
MLA
Copy
Yuan, Shaoren, et al. “Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles.” Molecules, vol. 27, no. 23, Nov. 2022, p. 8344. https://doi.org/10.3390/molecules27238344.