Journal of Organic Chemistry p. 5746 - 5758 (1989)
Update date:2022-08-05
Topics:
Weidner-Wells, Michele A.
DeCamp, Ann
Mazzocchi, Paul H.
The total syntheses of the pyrrolo<1,4>benzodiazepine antitumor antibiotics prothracarcin and DC-81 were realized using, as a key step, the photochemical <2δ + 2?> ring expansion of the appropriately substituted N-pentenylphthalimide to afford the corresponding pyrrolobenzazepinedione.Conversion of the photoproduct into the antibiotic skeleton was effected by transformation of the benzylic ketone into a carbinolamine via a Curtius rearrangement sequence.
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(1989)
