Directed ortho metalation - cross coupling connections. Remote lateral metalation - cyclization of 2-imino-2′-methyl biaryls to 9-aminophenanthrenes. A synthesis of the alkaloid piperolactam C

Directed ortho metalation - cross coupling connections. Remote lateral metalation - cyclization of 2-imino-2′-methyl biaryls to 9-aminophenanthrenes. A synthesis of the alkaloid piperolactam C

2-Imino-2′-methyl biaryls, conveniently available by Suzuki cross coupling protocol, undergo lithium diethyl amide-mediated metalation - cyclization to give 9-aminophenanthrenes (Table 1). The application of this new general methodology to the first synthesis of the alkaloid piperolactam C ( 9) is d...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 39; no. 9; pp. 961 - 964
Main Authors: Benesch, Lisbeth, Bury, Paul, Guillaneux, Denis, Houldsworth, Stephen, Wang, X., Snieckus, Victor
Format: Journal Article
Language:English
Published: Elsevier Ltd 26-02-1998
Online Access:Get full text
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Summary:2-Imino-2′-methyl biaryls, conveniently available by Suzuki cross coupling protocol, undergo lithium diethyl amide-mediated metalation - cyclization to give 9-aminophenanthrenes (Table 1). The application of this new general methodology to the first synthesis of the alkaloid piperolactam C ( 9) is described. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)10670-0