Issue 19, 2004

Evaluation of alternative approaches for the synthesis of macrocyclic bisindolylmaleimides

Abstract

Approaches for the synthesis of macrocyclic bisindolylmaleimides, in which the indole nitrogens are linked with a tether, are described. Two alternative approaches were investigated: macrocyclisation in either the ‘southern’ (by adding the tether to the bisindolylmaleimide ring system) or the ‘northern’ district. With two-, three- and four-atom tethers, both of these approaches were unsuccessful for a wide range of attempted macrocyclisation reactions (palladium-catalysed π-allyl substitution, ring-closing metathesis, McMurry reaction, iodocyclisation, formation of a silylene derivative, substitution of an α,ω-disubstituted electrophile). The failure of all of these reactions was ascribed to the strained nature of the target ring system. However, with longer tethers (six to ten atoms), the macrocycles could prepared using either a ring-closing metathesis reaction or by substitution of an α,ω-dibromide). Fourteen successful macrocyclisation reactions are described; deprotection gave eleven macrocyclic bisindolylmaleimides in which an imide substituent had been removed.

Graphical abstract: Evaluation of alternative approaches for the synthesis of macrocyclic bisindolylmaleimides

Article information

Article type
Paper
Submitted
05 Apr 2004
Accepted
10 Aug 2004
First published
10 Sep 2004

Org. Biomol. Chem., 2004,2, 2874-2883

Evaluation of alternative approaches for the synthesis of macrocyclic bisindolylmaleimides

S. Bartlett and A. Nelson, Org. Biomol. Chem., 2004, 2, 2874 DOI: 10.1039/B405010J

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