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Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives

Authorized Users Only
2011
Authors
Husinec, Suren
Savić, Vladimir
Simić, Milena R.
Tešević, Vele
Vidović, Dragoslav
Article (Published version)
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Abstract
Annulation processes of isoquinoline and p-carboline compounds have been investigated leading to synthetic routes for the preparation of 8-oxoprotoberberine derivatives. The key steps combined a diene formation/Diels-Alder cycloaddition reaction to afford the targeted polycyclic skeletons. Further oxidative transformations of the cycloadducts produced the 8-oxoprotoberberine type products. The alkaloids of this class are important natural products with a wide range of biological activity and the synthethic methodology described in this paper could prove to be useful for the preparation of the D-ring functionalised derivatives.
Keywords:
Isoquinoline / Annulations / 8-Oxoprotoberberine skeletons / Synthesis
Source:
Tetrahedron Letters, 2011, 52, 21, 2733-2736
Publisher:
  • Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
  • Computational design, synthesis and biological evaluation of new heterocyclic compounds as selective tumorogenesis inhibitors (RS-172009)
  • NTU (SPMS)
  • NTU (CBC)

DOI: 10.1016/j.tetlet.2011.03.085

ISSN: 0040-4039

WoS: 000290602100030

Scopus: 2-s2.0-79955483488
[ Google Scholar ]
9
9
URI
http://cherry.chem.bg.ac.rs/handle/123456789/1342
https://cer.ihtm.bg.ac.rs/handle/123456789/3505
http://farfar.pharmacy.bg.ac.rs/handle/123456789/1567
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Husinec, Suren
AU  - Savić, Vladimir
AU  - Simić, Milena R.
AU  - Tešević, Vele
AU  - Vidović, Dragoslav
PY  - 2011
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1342
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3505
UR  - http://farfar.pharmacy.bg.ac.rs/handle/123456789/1567
AB  - Annulation processes of isoquinoline and p-carboline compounds have been investigated leading to synthetic routes for the preparation of 8-oxoprotoberberine derivatives. The key steps combined a diene formation/Diels-Alder cycloaddition reaction to afford the targeted polycyclic skeletons. Further oxidative transformations of the cycloadducts produced the 8-oxoprotoberberine type products. The alkaloids of this class are important natural products with a wide range of biological activity and the synthethic methodology described in this paper could prove to be useful for the preparation of the D-ring functionalised derivatives.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron Letters
T1  - Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives
VL  - 52
IS  - 21
SP  - 2733
EP  - 2736
DO  - 10.1016/j.tetlet.2011.03.085
ER  - 
@article{
author = "Husinec, Suren and Savić, Vladimir and Simić, Milena R. and Tešević, Vele and Vidović, Dragoslav",
year = "2011",
abstract = "Annulation processes of isoquinoline and p-carboline compounds have been investigated leading to synthetic routes for the preparation of 8-oxoprotoberberine derivatives. The key steps combined a diene formation/Diels-Alder cycloaddition reaction to afford the targeted polycyclic skeletons. Further oxidative transformations of the cycloadducts produced the 8-oxoprotoberberine type products. The alkaloids of this class are important natural products with a wide range of biological activity and the synthethic methodology described in this paper could prove to be useful for the preparation of the D-ring functionalised derivatives.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron Letters",
title = "Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives",
volume = "52",
number = "21",
pages = "2733-2736",
doi = "10.1016/j.tetlet.2011.03.085"
}
Husinec, S., Savić, V., Simić, M. R., Tešević, V.,& Vidović, D.. (2011). Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives. in Tetrahedron Letters
Oxford : Pergamon-Elsevier Science Ltd., 52(21), 2733-2736.
https://doi.org/10.1016/j.tetlet.2011.03.085
Husinec S, Savić V, Simić MR, Tešević V, Vidović D. Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives. in Tetrahedron Letters. 2011;52(21):2733-2736.
doi:10.1016/j.tetlet.2011.03.085 .
Husinec, Suren, Savić, Vladimir, Simić, Milena R., Tešević, Vele, Vidović, Dragoslav, "Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives" in Tetrahedron Letters, 52, no. 21 (2011):2733-2736,
https://doi.org/10.1016/j.tetlet.2011.03.085 . .

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