O-Debenzylation of a Pyrrolo[2,1-c][1,4]benzodiazepine in the Presence of a Carbinolamine Functionality: Synthesis of DC-81
- 1 January 1990
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1990 (01) , 81-84
- https://doi.org/10.1055/s-1990-26795
Abstract
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.Keywords
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