Organic Letters, volume 10, issue 19, pages 4315-4318
Au(I)-Catalyzed Ring Expanding Cycloisomerizations: Total Synthesis of Ventricosene
Publication type: Journal Article
Publication date: 2008-08-30
Journal:
Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.2
ISSN: 15237060, 15237052
PubMed ID:
18759435
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
The gold(I)-catalyzed cycloisomerization of enynes containing an embedded cyclopropane unit leads selectively to the formation of ring systems containing the cyclopropylmethyl cation. A subsequent Wagner-Merwein shift provides diastereomerically pure fused cyclobutanes. The utility of this methodology for the rapid assembly of polycyclic ring systems is illustrated by the total synthesis of the angular triquinane ventricosene.
Top-30
Citations by journals
|
2
4
6
8
10
12
|
|
|
Organic Letters
12 publications, 7.32%
|
|
|
Journal of the American Chemical Society
10 publications, 6.1%
|
|
|
Angewandte Chemie - International Edition
9 publications, 5.49%
|
|
|
Angewandte Chemie
9 publications, 5.49%
|
|
|
Chemical Reviews
9 publications, 5.49%
|
|
|
Tetrahedron
7 publications, 4.27%
|
|
|
Chemistry - A European Journal
7 publications, 4.27%
|
|
|
Chemical Society Reviews
6 publications, 3.66%
|
|
|
Journal of Organic Chemistry
5 publications, 3.05%
|
|
|
Chemical Science
5 publications, 3.05%
|
|
|
Tetrahedron Letters
4 publications, 2.44%
|
|
|
ACS Catalysis
4 publications, 2.44%
|
|
|
Organic and Biomolecular Chemistry
4 publications, 2.44%
|
|
|
Chemical Communications
4 publications, 2.44%
|
|
|
Advanced Synthesis and Catalysis
3 publications, 1.83%
|
|
|
European Journal of Organic Chemistry
3 publications, 1.83%
|
|
|
Natural Product Reports
3 publications, 1.83%
|
|
|
Topics in Current Chemistry
3 publications, 1.83%
|
|
|
Russian Chemical Reviews
2 publications, 1.22%
|
|
|
Beilstein Journal of Organic Chemistry
2 publications, 1.22%
|
|
|
Israel Journal of Chemistry
2 publications, 1.22%
|
|
|
Chemistry - An Asian Journal
2 publications, 1.22%
|
|
|
Applied Catalysis B: Environmental
1 publication, 0.61%
|
|
|
Molecules
1 publication, 0.61%
|
|
|
Catalysts
1 publication, 0.61%
|
|
|
Nature Chemistry
1 publication, 0.61%
|
|
|
Bioorganic and Medicinal Chemistry Letters
1 publication, 0.61%
|
|
|
Coordination Chemistry Reviews
1 publication, 0.61%
|
|
|
Tetrahedron Asymmetry
1 publication, 0.61%
|
|
|
2
4
6
8
10
12
|
Citations by publishers
|
10
20
30
40
50
60
|
|
|
Wiley
58 publications, 35.37%
|
|
|
American Chemical Society (ACS)
42 publications, 25.61%
|
|
|
Royal Society of Chemistry (RSC)
24 publications, 14.63%
|
|
|
Elsevier
21 publications, 12.8%
|
|
|
Springer Nature
6 publications, 3.66%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
2 publications, 1.22%
|
|
|
Beilstein-Institut
2 publications, 1.22%
|
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
2 publications, 1.22%
|
|
|
Pleiades Publishing
1 publication, 0.61%
|
|
|
Thieme
1 publication, 0.61%
|
|
|
10
20
30
40
50
60
|
- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2008,2009,2010,2011,2012,2013,2014,2015,2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["","","","","","","","","","","","","","","","",""],"datasets":[{"label":"Citations number","data":[2,15,9,18,17,9,21,11,8,10,6,8,17,6,1,5,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["1.22","9.15","5.49","10.98","10.37","5.49","12.8","6.71","4.88","6.1","3.66","4.88","10.37","3.66","0.61","3.05","0.61"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Organic Letters","Journal of the American Chemical Society","Angewandte Chemie - International Edition","Angewandte Chemie","Chemical Reviews","Tetrahedron","Chemistry - A European Journal","Chemical Society Reviews","Journal of Organic Chemistry","Chemical Science","Tetrahedron Letters","ACS Catalysis","Organic and Biomolecular Chemistry","Chemical Communications","Advanced Synthesis and Catalysis","European Journal of Organic Chemistry","Natural Product Reports","Topics in Current Chemistry","Russian Chemical Reviews","Beilstein Journal of Organic Chemistry","Israel Journal of Chemistry","Chemistry - An Asian Journal","Applied Catalysis B: Environmental","Molecules","Catalysts","Nature Chemistry","Bioorganic and Medicinal Chemistry Letters","Coordination Chemistry Reviews","Tetrahedron Asymmetry"],"ids":[3315,4813,19215,25450,13718,3439,24708,20586,8697,9646,6133,4873,541,9073,3906,19472,15252,23927,23802,21928,17699,10120,18270,1770,3739,17228,8828,13437,23178],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/ex6KJoZujZOZFZh7jGfeHauiftuB3CI7iwJVFRDg_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp"],"datasets":[{"label":"","data":[12,10,9,9,9,7,7,6,5,5,4,4,4,4,3,3,3,3,2,2,2,2,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[7.32,6.1,5.49,5.49,5.49,4.27,4.27,3.66,3.05,3.05,2.44,2.44,2.44,2.44,1.83,1.83,1.83,1.83,1.22,1.22,1.22,1.22,0.61,0.61,0.61,0.61,0.61,0.61,0.61],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Wiley","American Chemical Society (ACS)","Royal Society of Chemistry (RSC)","Elsevier","Springer Nature","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii","Beilstein-Institut","Multidisciplinary Digital Publishing Institute (MDPI)","Pleiades Publishing","Thieme"],"ids":[11,40,123,17,8,9422,6139,202,101,135],"codes":[0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/ex6KJoZujZOZFZh7jGfeHauiftuB3CI7iwJVFRDg_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp"],"datasets":[{"label":"","data":[58,42,24,21,6,2,2,2,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[35.37,25.61,14.63,12.8,3.66,1.22,1.22,1.22,0.61,0.61],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartiles":{"type":"bar","data":{"show":true,"labels":[2008,2009,2010,2011,2012,2013,2014,2015,2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[1,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0],"percentage":["0.61","0","0","0","0","0","0","0.61","0","0","0","0","0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,2,0,1,0,0,1,0,0,0,0,0,0,0,0,0,0],"percentage":["0","1.22","0","0.61","0","0","0.61","0","0","0","0","0","0","0","0","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,2,2,2,0,2,0,0,2,2,0,1,4,1,0,0,0],"percentage":["0","1.22","1.22","1.22","0","1.22","0","0","1.22","1.22","0","0.61","2.44","0.61","0","0","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,10,6,11,11,6,12,6,5,6,6,7,13,4,1,4,1],"percentage":["0.61","6.1","3.66","6.71","6.71","3.66","7.32","3.66","3.05","3.66","3.66","4.27","7.93","2.44","0.61","2.44","0.61"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,1,1,4,6,1,8,4,1,2,0,0,0,1,0,1,0],"percentage":["0","0.61","0.61","2.44","3.66","0.61","4.88","2.44","0.61","1.22","0","0","0","0.61","0","0.61","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by SCImago per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartilesWs":{"type":"bar","data":{"show":true,"labels":[2008,2009,2010,2011,2012,2013,2014,2015,2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0,0,0,1,0,0,0,0,0,0,0,0,0],"percentage":["0","0","0","0","0","0","0","0.61","0","0","0","0","0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,2,2,1,0,1,1,0,0,1,0,1,3,1,0,0,0],"percentage":["0","1.22","1.22","0.61","0","0.61","0.61","0","0","0.61","0","0.61","1.83","0.61","0","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,4,1,2,4,2,2,1,4,4,2,1,1,2,1,1,0],"percentage":["0","2.44","0.61","1.22","2.44","1.22","1.22","0.61","2.44","2.44","1.22","0.61","0.61","1.22","0.61","0.61","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,6,5,9,7,5,9,5,3,3,4,5,11,2,0,2,1],"percentage":["0.61","3.66","3.05","5.49","4.27","3.05","5.49","3.05","1.83","1.83","2.44","3.05","6.71","1.22","0","1.22","0.61"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[1,3,1,6,6,1,9,4,1,2,0,1,2,1,0,2,0],"percentage":["0.61","1.83","0.61","3.66","3.66","0.61","5.49","2.44","0.61","1.22","0","0.61","1.22","0.61","0","1.22","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by WoS per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Sethofer S. G. et al. Au(I)-Catalyzed Ring Expanding Cycloisomerizations: Total Synthesis of Ventricosene // Organic Letters. 2008. Vol. 10. No. 19. pp. 4315-4318.
GOST all authors (up to 50)
Copy
Sethofer S. G., Staben S. T., Hung O. Y., Toste F. D. Au(I)-Catalyzed Ring Expanding Cycloisomerizations: Total Synthesis of Ventricosene // Organic Letters. 2008. Vol. 10. No. 19. pp. 4315-4318.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ol801760w
UR - https://doi.org/10.1021/ol801760w
TI - Au(I)-Catalyzed Ring Expanding Cycloisomerizations: Total Synthesis of Ventricosene
T2 - Organic Letters
AU - Sethofer, Steven G.
AU - Hung, Olivia Y
AU - Staben, Steven T
AU - Toste, F. Dean
PY - 2008
DA - 2008/08/30 00:00:00
PB - American Chemical Society (ACS)
SP - 4315-4318
IS - 19
VL - 10
PMID - 18759435
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex
Copy
@article{2008_Sethofer,
author = {Steven G. Sethofer and Olivia Y Hung and Steven T Staben and F. Dean Toste},
title = {Au(I)-Catalyzed Ring Expanding Cycloisomerizations: Total Synthesis of Ventricosene},
journal = {Organic Letters},
year = {2008},
volume = {10},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/ol801760w},
number = {19},
pages = {4315--4318},
doi = {10.1021/ol801760w}
}
Cite this
MLA
Copy
Sethofer, Steven G., et al. “Au(I)-Catalyzed Ring Expanding Cycloisomerizations: Total Synthesis of Ventricosene.” Organic Letters, vol. 10, no. 19, Aug. 2008, pp. 4315-4318. https://doi.org/10.1021/ol801760w.