β-Carboline Alkaloids 9 [1]. Total Synthesis of the β-Carboline Alkaloids Arenarine A and (±)Arenarine B
The first total synthesis of the β-carboline alkaloids arenarine A (1) and arenarine B (2) is described. Methanolysis of the α-bromoketone 9 gives 1 in good yield. Alternatively 1 can be obtained from the diazoketone 11 with boron trifluoride/methanol in poor yield. Reduction of 1 with sodium borohydride gives racemic arenarine B (2). Regioselective homolytic methylation of norharmane (4) with tert-butyl hydroperoxide/ferrous sulfate gives the alkaloid harmane (6).
Bracher, Franz,Puzik, Andreas
p. 173 - 176
(2007/10/03)
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