Journal of the American Chemical Society, volume 145, issue 4, pages 2584-2595
Total Syntheses of Nominal and Actual Prorocentin
Publication type: Journal Article
Publication date: 2023-01-18
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
The dinoflagellate-derived polyether prorocentin is a co-metabolite of the archetypical serine/threonine phosphatase inhibitor okadaic acid. Whereas a structural relationship cannot be missed and a biosynthetic link was proposed, it is currently unknown whether there is any parallel in the bioactivity profile of these natural products. However, it was insinuated in the past that the structure assigned to prorocentin might need to be revised. Indeed, re-examination of the published spectra cast doubts as to the constitution of the fused/spirotricyclic BCD-ring system in the core. To clarify this issue, a flexible synthesis blueprint was devised that allowed us to obtain the originally proposed structure as well as the most plausible amended structure. The key to success was late-stage gold-catalyzed spirocyclization reactions that furnished the isomeric central segments with excellent selectivity. The lexicon of catalytic transformations used to make the required cyclization precursors comprised a titanium-mediated ester methylenation/metathesis cascade, a rare example of a gold-catalyzed allylic substitution, and chain extensions via organocatalytic asymmetric aldehyde propargylation. A wing sector to be attached to the isomeric cores was obtained by Krische allylation, followed by a superbly selective cobalt-catalyzed oxidative cyclization of the resulting di-unsaturated alcohol with the formation of a 2,5-trans-disubstituted tetrahydrofuran; the remaining terminal alkene was elaborated into an appropriate handle for fragment coupling by platinum-catalyzed asymmetric diboration/oxidation. The assembly of the different building blocks to the envisaged isomeric target compounds proved that the structure of prorocentin needs to be revised as disclosed herein.
Top-30
Citations by journals
|
1
2
|
|
|
Organic Letters
2 publications, 18.18%
|
|
|
Journal of the American Chemical Society
2 publications, 18.18%
|
|
|
Synfacts
1 publication, 9.09%
|
|
|
ACS Catalysis
1 publication, 9.09%
|
|
|
Arabian Journal of Chemistry
1 publication, 9.09%
|
|
|
Natural Product Reports
1 publication, 9.09%
|
|
|
Chemistry - A European Journal
1 publication, 9.09%
|
|
|
Russian Chemical Reviews
1 publication, 9.09%
|
|
|
1
2
|
Citations by publishers
|
1
2
3
4
5
|
|
|
American Chemical Society (ACS)
5 publications, 45.45%
|
|
|
Thieme
1 publication, 9.09%
|
|
|
Elsevier
1 publication, 9.09%
|
|
|
Royal Society of Chemistry (RSC)
1 publication, 9.09%
|
|
|
Wiley
1 publication, 9.09%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 9.09%
|
|
|
1
2
3
4
5
|
- 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":[2023,2024],"ids":[0,0],"codes":[0,0],"imageUrls":["",""],"datasets":[{"label":"Citations number","data":[5,6],"backgroundColor":["#3B82F6","#3B82F6"],"percentage":["45.45","54.55"],"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","Synfacts","ACS Catalysis","Arabian Journal of Chemistry","Natural Product Reports","Chemistry - A European Journal","Russian Chemical Reviews"],"ids":[3315,4813,25513,4873,18459,15252,24708,23802],"codes":[0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/9z7b0TQJNgUxZHYXLrTmbnjJn9y5iq56Wxtqb1Lv_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[2,2,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[18.18,18.18,9.09,9.09,9.09,9.09,9.09,9.09],"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":["American Chemical Society (ACS)","Thieme","Elsevier","Royal Society of Chemistry (RSC)","Wiley","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii"],"ids":[40,135,17,123,11,9422],"codes":[0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[5,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[45.45,9.09,9.09,9.09,9.09,9.09],"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":[2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0],"percentage":["0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0],"percentage":["0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,0],"percentage":["0","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[3,6],"percentage":["27.27","54.55"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[2,0],"percentage":["18.18","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":[2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0],"percentage":["0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0],"percentage":["0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,2],"percentage":["0","18.18"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[3,4],"percentage":["27.27","36.36"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[2,0],"percentage":["18.18","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
Zachmann R. J. et al. Total Syntheses of Nominal and Actual Prorocentin // Journal of the American Chemical Society. 2023. Vol. 145. No. 4. pp. 2584-2595.
GOST all authors (up to 50)
Copy
Zachmann R. J., Yahata K., Holzheimer M., Jarret M., Wirtz C., Fürstner A. Total Syntheses of Nominal and Actual Prorocentin // Journal of the American Chemical Society. 2023. Vol. 145. No. 4. pp. 2584-2595.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jacs.2c12529
UR - https://doi.org/10.1021/jacs.2c12529
TI - Total Syntheses of Nominal and Actual Prorocentin
T2 - Journal of the American Chemical Society
AU - Zachmann, Raphael J
AU - Yahata, Kenzo
AU - Holzheimer, Mira
AU - Jarret, Maxime
AU - Wirtz, Cornelia
AU - Fürstner, Alois
PY - 2023
DA - 2023/01/18 00:00:00
PB - American Chemical Society (ACS)
SP - 2584-2595
IS - 4
VL - 145
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex
Copy
@article{2023_Zachmann,
author = {Raphael J Zachmann and Kenzo Yahata and Mira Holzheimer and Maxime Jarret and Cornelia Wirtz and Alois Fürstner},
title = {Total Syntheses of Nominal and Actual Prorocentin},
journal = {Journal of the American Chemical Society},
year = {2023},
volume = {145},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/jacs.2c12529},
number = {4},
pages = {2584--2595},
doi = {10.1021/jacs.2c12529}
}
Cite this
MLA
Copy
Zachmann, Raphael J., et al. “Total Syntheses of Nominal and Actual Prorocentin.” Journal of the American Chemical Society, vol. 145, no. 4, Jan. 2023, pp. 2584-2595. https://doi.org/10.1021/jacs.2c12529.