Borylation via Iridium catalysed C-H activation: a new concise route to duocarmycin derivatives

The synthesis of the ethyl ester analogue of the ultapotent antitumour antibiotic seco-duocarmycin SA has been achieved in eleven linear steps from commercially available starting materials. The DSA alkylation subunit can be made in ten linear steps from the same precursor. The route involves CH activation at the equivalent of the C7 position on indole leading to a borylated intermediate 9 that is stable enough for coupling reactions but can be easily converted to the free hydroxyl analogue.