Asymmetric Total Syntheses of (+)-Davisinol and (+)-18-Benzoyldavisinol: A HAT-Initiated Transannular Redox Radical Approach
Publication type: Journal Article
Publication date: 2021-07-09
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
34240855
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
The first and asymmetric total syntheses of two C11-oxygenated hetisine-type diterpenoid alkaloids, namely, (+)-davisinol and (+)-18-benzoyldavisinol, is described. The concise synthetic approach features a HAT-initiated transannular redox radical cyclization, an ODI-Diels-Alder cycloaddition, and an acylative kinetic resolution. By incorporating an efficient late-stage assembly of the azabicycle, our strategy would streamline the synthetic design of C20-diterpenoid alkaloids and pave the way for their modular syntheses.
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Metrics
33
Total citations:
33
Citations from 2024:
17
(53.13%)
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GOST
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Yu K. et al. Asymmetric Total Syntheses of (+)-Davisinol and (+)-18-Benzoyldavisinol: A HAT-Initiated Transannular Redox Radical Approach // Journal of the American Chemical Society. 2021. Vol. 143. No. 28. pp. 10576-10581.
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Yu K., Yao F., Zeng Q., Xie H., Ding H. Asymmetric Total Syntheses of (+)-Davisinol and (+)-18-Benzoyldavisinol: A HAT-Initiated Transannular Redox Radical Approach // Journal of the American Chemical Society. 2021. Vol. 143. No. 28. pp. 10576-10581.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jacs.1c05703
UR - https://doi.org/10.1021/jacs.1c05703
TI - Asymmetric Total Syntheses of (+)-Davisinol and (+)-18-Benzoyldavisinol: A HAT-Initiated Transannular Redox Radical Approach
T2 - Journal of the American Chemical Society
AU - Yu, Kuan
AU - Yao, Fengjie
AU - Zeng, Qingrui
AU - Xie, Hujun
AU - Ding, Hanfeng
PY - 2021
DA - 2021/07/09
PB - American Chemical Society (ACS)
SP - 10576-10581
IS - 28
VL - 143
PMID - 34240855
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2021_Yu,
author = {Kuan Yu and Fengjie Yao and Qingrui Zeng and Hujun Xie and Hanfeng Ding},
title = {Asymmetric Total Syntheses of (+)-Davisinol and (+)-18-Benzoyldavisinol: A HAT-Initiated Transannular Redox Radical Approach},
journal = {Journal of the American Chemical Society},
year = {2021},
volume = {143},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/jacs.1c05703},
number = {28},
pages = {10576--10581},
doi = {10.1021/jacs.1c05703}
}
Cite this
MLA
Copy
Yu., Kuan, et al. “Asymmetric Total Syntheses of (+)-Davisinol and (+)-18-Benzoyldavisinol: A HAT-Initiated Transannular Redox Radical Approach.” Journal of the American Chemical Society, vol. 143, no. 28, Jul. 2021, pp. 10576-10581. https://doi.org/10.1021/jacs.1c05703.