The next consideration regarded which proximal and remote functionality would be the optimal choice for the substrate given synthetic accessibility, predicted efficiency, and utility in accessing a variety of clovanes. A selection of substrates from over 100 predictions is shown in Figure to illustrate the planning considerations that were made. For example, the introduction of carbonyl groups stabilizing the radical intermediate in triketone 13, the protection of carbonyl group adjacent to the radical center in 14, and the introduction of substituents at the site of radical cyclization in 15, have predicted yields that are qualitatively in line with expert intuition. Compounds 16 and 17, which would readily lead to other clovane natural products, are predicted to cyclize in synthetically useful yields. When 22 was subjected to optimized radical cyclization conditions (AIBN, n-Bu 3 SnH), clovan-2,9-dione (1) was produced in 45% yield. This result is in excellent agreement with the predicted yield of 46%. Since the literature examples used to train the NNET model are generally optimized yields, the predictions are for optimized yields as well. The successful realization of this radical cyclization resulted in a 5-step synthesis of 1, which is significantly more efficient than the previously disclosed 15-step strategy . As shown in Figure , the NNET model predicted the feasibility of radical cyclization from 27 to form 28 (predicted yield: 51%). The experimental success of this transformation enabled the first total syntheses of rumphellclovane A (30) and canangaterpene II (2) (29) in 8 steps from commercially available 18. The key elements of the synthesis are selective reduction of 20 to form 24, a Mitsunobu reaction to invert the stereochemistry to 25, and a late-stage Baeyer-Villiger and selective transesterification (28 to 30). The structure of canangaterpene II (2) was revised from the previously proposed structure based on biosynthetic considerations , NMR calculations, and our synthesis of the revised structure (see SI for details).