Synthetic Studies of 7-Oxygenated Aporphine Alkaloids: Preparation of (−)-Oliveroline, (−)-Nornuciferidine, and Derivatives
Publication type: Journal Article
Publication date: 2015-02-24
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
25710592
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
7-Oxygenated aporphines 1-6 possessing anti-configurations have previously been reported. In order to explore their bioactivities, a synthesis was established by utilizing a diastereoselective reductive acid-mediated cyclization followed by palladium-catalyzed ortho-arylations. Moderate XPhos precatalyst loading (10 mol %) and short reaction times (30 min) were sufficient to mediate the arylations. Alkaloids 1-5 were successfully prepared, while (-)-artabonatine A was revised to syn-isomer 30. Consequently, (-)-artabonatine E likely also has a syn-configuration (31).
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Total citations:
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Citations from 2024:
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GOST
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Ku A. F., Cuny G. D. Synthetic Studies of 7-Oxygenated Aporphine Alkaloids: Preparation of (−)-Oliveroline, (−)-Nornuciferidine, and Derivatives // Organic Letters. 2015. Vol. 17. No. 5. pp. 1134-1137.
GOST all authors (up to 50)
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Ku A. F., Cuny G. D. Synthetic Studies of 7-Oxygenated Aporphine Alkaloids: Preparation of (−)-Oliveroline, (−)-Nornuciferidine, and Derivatives // Organic Letters. 2015. Vol. 17. No. 5. pp. 1134-1137.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.5b00007
UR - https://doi.org/10.1021/acs.orglett.5b00007
TI - Synthetic Studies of 7-Oxygenated Aporphine Alkaloids: Preparation of (−)-Oliveroline, (−)-Nornuciferidine, and Derivatives
T2 - Organic Letters
AU - Ku, Angela F
AU - Cuny, Gregory D
PY - 2015
DA - 2015/02/24
PB - American Chemical Society (ACS)
SP - 1134-1137
IS - 5
VL - 17
PMID - 25710592
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2015_Ku,
author = {Angela F Ku and Gregory D Cuny},
title = {Synthetic Studies of 7-Oxygenated Aporphine Alkaloids: Preparation of (−)-Oliveroline, (−)-Nornuciferidine, and Derivatives},
journal = {Organic Letters},
year = {2015},
volume = {17},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/acs.orglett.5b00007},
number = {5},
pages = {1134--1137},
doi = {10.1021/acs.orglett.5b00007}
}
Cite this
MLA
Copy
Ku, Angela F., and Gregory D Cuny. “Synthetic Studies of 7-Oxygenated Aporphine Alkaloids: Preparation of (−)-Oliveroline, (−)-Nornuciferidine, and Derivatives.” Organic Letters, vol. 17, no. 5, Feb. 2015, pp. 1134-1137. https://doi.org/10.1021/acs.orglett.5b00007.