(+)-Oxo-tomaymycin,
a naturally occurring substance of the pyrrolo-1,4-benzodiazepine
family, was synthesized using a short and efficient route. The key
construction of the seven-membered ring by amide bond formation was
realized via a chemoselective Ar-NO2 reduction using TiCl3 under acidic conditions, followed by a spontaneous cyclization.
This synthesis was easily scaled up to 80 g, and it should be amenable
to the production of larger quantities.
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