Journal of Organic Chemistry p. 2170 - 2178 (1989)
Update date:2022-08-02
Topics: Oxidation DDQ Indole 4-Alkoxy-β-carbolines Crenatine 1-Methoxycanthin-6-one
Hagen, Timothy J.
Narayanan, Krishnaswamy
Names, Jeffrey
Cook, James M.
The seven-step synthesis of the cytotoxic, antileukemic alkaloid 1-methoxycanthin-6-one (2b) is described.The pivotal steps are represented by the oxidation (DDQ, aqueous THF, room temperature) of 1-(methoxycarbonyl)-1,2,3,4-tetrahydro-β-carboline (10) to provide the 4-oxo-substituted derivative 14 in 78percent yield, and conversion of the 4-oxo analogue 7 into 4-methoxy-1-alkyl-β-carboline (23) via a methoxylation-oxidation process
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Doi:10.1007/BF01045302
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(2012)Doi:10.1134/S1068162012050020
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(2012)Doi:10.1016/S0040-4039(00)91848-3
(1992)