Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives
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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-Asymmetry, 2011, 52, 21, 2733-2736
- Pergamon-Elsevier Science Ltd, Oxford