Total Synthesis of (±)-Armepavines and (±)-Nuciferines From (2-Nitroethenyl)benzene Derivatives
Chia-Fu Chang
1
,
Chu-Yun Huang
1
,
Yu Chao Huang
1
,
Kuan-Yu Lin
1
,
Yean-Jang Lee
1
,
Chau-Jong Wang
2
2
b Institute of Biochemistry , Chung Shan Medical University , Taichung, Taiwan
|
Publication type: Journal Article
Publication date: 2010-11-03
scimago Q3
wos Q3
SJR: 0.322
CiteScore: 4.3
Impact factor: 1.8
ISSN: 00397911, 15322432
Organic Chemistry
Abstract
A concise route to armepavine 1 and nuciferine 2 and 3, which can be isolated from the leaves of Nelumbo nucifera (Nymphaceae), has been achieved in which the longest linear sequence is only six steps from commercially available benzaldehyde in 28%, 21%, and 20% overall yield, respectively. The key transformations in the synthesis are the radical cyclization of aryl bromide with Bu3SnH and the Pictet–Spengler reaction of N-substituted amine with aldehyde.
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15
Total citations:
15
Citations from 2025:
1
(6.67%)
Cite this
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MLA
Cite this
GOST
Copy
Chang C. et al. Total Synthesis of (±)-Armepavines and (±)-Nuciferines From (2-Nitroethenyl)benzene Derivatives // Synthetic Communications. 2010. Vol. 40. No. 23. pp. 3452-3466.
GOST all authors (up to 50)
Copy
Chang C., Huang C., Huang Yu. C., Lin K., Lee Y., Wang C. Total Synthesis of (±)-Armepavines and (±)-Nuciferines From (2-Nitroethenyl)benzene Derivatives // Synthetic Communications. 2010. Vol. 40. No. 23. pp. 3452-3466.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1080/00397910903435411
UR - https://doi.org/10.1080/00397910903435411
TI - Total Synthesis of (±)-Armepavines and (±)-Nuciferines From (2-Nitroethenyl)benzene Derivatives
T2 - Synthetic Communications
AU - Chang, Chia-Fu
AU - Huang, Chu-Yun
AU - Huang, Yu Chao
AU - Lin, Kuan-Yu
AU - Lee, Yean-Jang
AU - Wang, Chau-Jong
PY - 2010
DA - 2010/11/03
PB - Taylor & Francis
SP - 3452-3466
IS - 23
VL - 40
SN - 0039-7911
SN - 1532-2432
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2010_Chang,
author = {Chia-Fu Chang and Chu-Yun Huang and Yu Chao Huang and Kuan-Yu Lin and Yean-Jang Lee and Chau-Jong Wang},
title = {Total Synthesis of (±)-Armepavines and (±)-Nuciferines From (2-Nitroethenyl)benzene Derivatives},
journal = {Synthetic Communications},
year = {2010},
volume = {40},
publisher = {Taylor & Francis},
month = {nov},
url = {https://doi.org/10.1080/00397910903435411},
number = {23},
pages = {3452--3466},
doi = {10.1080/00397910903435411}
}
Cite this
MLA
Copy
Chang, Chia-Fu, et al. “Total Synthesis of (±)-Armepavines and (±)-Nuciferines From (2-Nitroethenyl)benzene Derivatives.” Synthetic Communications, vol. 40, no. 23, Nov. 2010, pp. 3452-3466. https://doi.org/10.1080/00397910903435411.