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β‐Carboline alkaloids 9 [1]. Total synthesis of the β‐carboline alkaloids arenarine A and (±)arenarine B
Author(s) -
Bracher Franz,
Puzik Andreas
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410206
Subject(s) - chemistry , boron trifluoride , sodium borohydride , yield (engineering) , regioselectivity , alkaloid , methanol , organic chemistry , chelerythrine , stereochemistry , enzyme , catalysis , materials science , protein kinase c , metallurgy
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).