Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives
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 / SynthesisSource:
Tetrahedron-Asymmetry, 2011, 52, 21, 2733-2736Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
- Computational design, synthesis and biological evaluation of new heterocyclic compounds as selective tumorogenesis inhibitors (RS-MESTD-Basic Research (BR or ON)-172009)
- NTU (CBC)
DOI: 10.1016/j.tetlet.2011.03.085
ISSN: 0040-4039
WoS: 000290602100030
Scopus: 2-s2.0-79955483488
Collections
Institution/Community
PharmacyTY - JOUR AU - Husinec, Suren AU - Savić, Vladimir AU - Simić, Milena AU - Tešević, Vele AU - Vidović, Dragoslav PY - 2011 UR - https://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 - Pergamon-Elsevier Science Ltd, Oxford T2 - Tetrahedron-Asymmetry 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 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 = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Tetrahedron-Asymmetry", 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., Tešević, V.,& Vidović, D.. (2011). Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives. in Tetrahedron-Asymmetry Pergamon-Elsevier Science Ltd, Oxford., 52(21), 2733-2736. https://doi.org/10.1016/j.tetlet.2011.03.085
Husinec S, Savić V, Simić M, Tešević V, Vidović D. Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives. in Tetrahedron-Asymmetry. 2011;52(21):2733-2736. doi:10.1016/j.tetlet.2011.03.085 .
Husinec, Suren, Savić, Vladimir, Simić, Milena, Tešević, Vele, Vidović, Dragoslav, "Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives" in Tetrahedron-Asymmetry, 52, no. 21 (2011):2733-2736, https://doi.org/10.1016/j.tetlet.2011.03.085 . .