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Isoquinuclidine synthesis by homoallylic radical rearrangement. Conditions: (a) (i) NBS (4.0 equiv), acetone/H2O (4:1 v/v), 0 to 25 °C, 3 days; (ii) BzCl (1.5 equiv), DMAP (0.5 equiv), TEA (5.0 equiv), CH2Cl2, 25 °C, 15 h, 43 %; (b) azobisisobutyronitrile (AIBN) (0.1 equiv), Bu3SnH (1.6 equiv), benzene, reflux, 5 h, 73 %; (c) (i) TFA (33 equiv), CH2Cl2, 25 °C, 1 h, (ii) 37 % aq CH2O (11 equiv), NaBH3CN (8.2 equiv), MeCN, 25 °C, 1.5 h, 61 %.
