Chemistry of Natural Compounds p. 479 - 483 (1992)
Update date:2022-08-03
Topics:
Mustafin, A. G.
Khalilov, I. N.
Tal'vinskii, E. V.
Abdrakhmanov, I. B.
Spirikhin, L. V.
Tolstikov, G. A.
A convenient method is proposed for the synthesis of the alkaloid ellipticine, which possesses a pronounced antitumoral activity.The interaction of 3-bromocyclohexene (1 equiv.) and 2,5-xylylidine (4 equiv., 150 deg C, 5 h) gave a mixture of hexa- and tetrahydrocarbazoles which was dehydrogenated in the presence of Pd/C to the key synthon 1,4-dimethylcarbazole.The formylation of the carbazole by the Vilsmeier-Haack reaction, interaction with 2,2-diethoxyethylamine, and reduction of the imine formed over Raney nickel led to 3-(2,2-diethoxyethylaminomethyl)-1,4-dimethylcarbazole, the boiling of the N-tosylate of which gave ellipticine in high yield.
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