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β-Carboline alkaloids 9 [1]. Total synthesis of the β-carboline alkaloids arenarine A and (±)arenarine B

✍ Scribed by Franz Bracher; Andreas Puzik

Publisher: Journal of Heterocyclic Chemistry
Year: 2004
Tongue: English
Weight: 128 KB
Volume: 41
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570410206

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✦ Synopsis

Abstract

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).

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