Alkaloids of the Australian Rutaceae: Medicosma cunninghamii Hook. F

Australian Journal of Chemistry
1953.0

Abstract

The bark of Medicosma cunninghamii Hook. f. contains approximately 0.06 per cent. of an alkaloid C17H15O3N which has been named medicosmine and shown to be a 2,3-furoquinoline with a dimethylpyran ring fused in either the 5,6- or 6,7-positions (III or IV). It has been degraded to acetone, acetaldehyde, and a phenol which when methylated and oxidized gives 6-methoxy-4-hydroxy-1-methyl-2-quinolone, and 6- and 7-methoxy-4-hydroxy-1-methyl-2-quinolones have been synthesized for comparison. A dihydropyrano-4-methoxy -3-ethyl-2-quinoone is formed by hydrogenolysis of the furane ring. Further examples are reported of the preparation of isatins from 3-nitroso-2,4- dihydroxyquinolines. © 1953, CSIRO. All rights reserved.

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