Abstract
The photocyclization of substituted 2,3-diaryl-Δ 2 -pyrroline-4,5-diones, with a forced cisstilbene geometry, afforded the corresponding phenanthrene derivatives. Concomitant photoreduction of the C-4 carbonyl group to methylene has been observed when triethylamine was used as acid scavenger. The role of the amine in the photocyclization and photoreduction steps is discussed in terms of the results obtained with different amines (triethylamine, pyridine, and tert-butylamine). The naturally occurring oxoglaucine, lysicamine, and dicentrinone have been synthesized in good to acceptable yields by Fremy's salt oxidation of the photocyclized products. © 1982, American Chemical Society. All rights reserved.
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