With the trained NNET model, different disconnections corresponding to different synthetic routes to clovan-2,9-dione (1) were evaluated (Figure ). The predicted yields of 6-endo-trig radical cyclizations from precursors 7, 8, and 9 are 46%, 46%, and 34%, respectively. The synthetically useful yield predicted for compound 7 is expected as such a disconnection with a polarized alkene is the conventional strategy for eliciting the 6-endo mode of cyclization. Although conventional logic would have discouraged the selection of 8 and 9 due to limited available precedent for cyclizations of this type , the model's encouraging predictions for 8 and 9 mitigated that concern and neutralized any perceived benefit to the lower risk strategy via 7. Finally, compound 8 was selected, as 8 has a comparable predicted yield and represents a more innovative disconnection (9) that leads to greater synthetic accessibility .