“…Using the procedure described for 29a, tricyclic ketone 22 (400 mg, 1.3 mmol) yielded a residue that was purified by chromatography on silica gel (20 g) using ether, and then crystallized from hexane to give 241 mg (79%) of 29b: mp 103-104 "C; IR (CH2C12) 3395, 1680, 1590 cm-I; NMR (CDC13) 6 1.26 (d, I , J = 8 Hz), 1. 5-2.0 (m, 9), 1.8-3.0 (m, 9), and 4.9-6.0 ppm (m, 4); mass spectrum m/e (re1 intensity) 164 (loo), 119 (52) endo-6-Cyano-2-methyI-6-(4-methylpent-3-en-l-yl)bicy~lo-[3.l.lpept-2-ene (30b). Using the procedure described for 30a, bicyclic amide 29b (210 mg, 0.9 mmol) furnished 153 mg (79%) of liquid 30b IR (CC14) 2230 cm-l; NMR (CDC13) 6 1.40 (d, 1, J = 8 Hz), 1.6-2.0 (m, 9), 1.85-2.9 (m, 9), and 4.9-5.6 ppm (m, 2).…”