Abstract
A simple total synthesis of the quinoline alkaloid, orixiarine was achieved from N-methylaniline and 1-bromo-3-methyl-2-butanone.
Highlights
A hemiterpenoid quinoline alkaloid, named orixiarine (Graph 1) was isolated from Skimmia laureola (Rutaceae), which is an aromatic gregarious evergreen shrub found in Western Himalayas and Kashmir [1,2]
Our program of synthesis of quinoline alkaloids, in particular the hemiterpenoid quinoline alkaloid [6] was achieved with a multi-step protocol and in comparatively less yield
We report our investigations which have resulted in a four-step, convenient total synthesis of orixiarine starting from N-methylaniline (2)
Summary
A hemiterpenoid quinoline alkaloid, named orixiarine (Graph 1) was isolated from Skimmia laureola (Rutaceae), which is an aromatic gregarious evergreen shrub found in Western Himalayas and Kashmir [1,2]. Our program of synthesis of quinoline alkaloids, in particular the hemiterpenoid quinoline alkaloid [6] was achieved with a multi-step protocol and in comparatively less yield. We report our investigations which have resulted in a four-step, convenient total synthesis of orixiarine starting from N-methylaniline (2). Compound 5 on treatment with p-methyltoluenesulphonate and potassium carbonate yielded the final product 1 which on analysis by 1H-NMR, 13C-NMR and mass spectra, is found to be identical with that isolated from Skimmia laureola [1] (Scheme 1)
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