Premium
General Au‐Catalyzed Benzannulation Towards Naturally Occurring Carbazole Alkaloids from Methoxypropadiene
Author(s) -
Kong Wangqing,
Fu Chunling,
Ma Shengming
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102251
Subject(s) - carbazole , catalysis , aldehyde , chemistry , prenylation , selectivity , combinatorial chemistry , organic chemistry , medicinal chemistry , enzyme
Accessible alkaloids : Naturally occurring carbazole alkaloids, such as clauszoline‐K, ‐L, ‐M, and ‐N, 3‐formyl‐7‐hydroxycarbazole, and siamenol, were synthesized through a gold‐catalyzed cyclization reaction of 1‐(indol‐2‐yl)‐2‐methoxy‐2,3‐allenols, which are readily available from indolecarbaldehydes and methoxypropadiene (see scheme; R 1 =Me, carboxylic acid/ester, or aldehyde; R 2 =prenyl or H; R 3 =H or Me). The reaction demonstrates atom economy, high selectivity, and high yields, mostly with catalytic reactions.