Synthesis 1990; 1990(1): 81-84
DOI: 10.1055/s-1990-26795
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O-Debenzylation of a Pyrrolo[2,1-c][1,4]benzodiazepine in the Presence of a Carbinolamine Functionality: Synthesis of DC-81

David E. Thurston* , Varanasi S. Murty, David R. Langley, Gary B. Jones
  • *Division of Medicinal Chemistry, School of Pharmacy, Portsmouth Polytechnic, King Henry I Street, Hants, PO1 2DZ, England
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17. September 2002 (online)

In contrast to other methods of reduction, catalytic transfer hydrogenation allows debenzylation of a phenolic hydroxyl in a carbinolamine-containing pyrrolo[2,1-c][1,4]benzodiazepine, while leaving the biologically-important carbinolamine moiety intact. This has been demonstrated by synthesis of the naturally occurring anti-tumour antibiotic DC-81 (10). An efficient synthesis of 4-benzyloxy-5-methoxy-2-nitrobenzoic acid (5), an important intermediate in the production of certain pyrrolobenzodiazepine antitumour agents, is also reported.