[Synthesis]
The general procedure for the synthesis of 3,7-dimethylocta-1,6-diene and bicyclo[2.2.1]hept-5-ene-2-carbonitrile from the compound (CAS:67403-76-3) and dicycloheptadiene was as follows: to a 4 mL screw-capped vial in an argon-protected glove box were added sequentially the compound 69 (82.6 mg, 0.50 mmol), norepiglottidiene 8 (51 μL, 0.5 mmol), hexane solution of 1.0 M AIMe2Cl (50 μL, 10.0 mol%, 0.05 mmol), Ni(COD)2 (3.45 mg, 2.5 mol%, 12.5 μmol), and DPEphos (6.75 mg, 2.5 mol%, 12.5 μmol) in THF ( 1.0 mL) solution. The vials were removed from the glove box and the reaction temperature was controlled at 28°C. The reaction mixture was stirred at 28 °C for 16 h and then concentrated under reduced pressure. The residue was purified by silica gel fast column chromatography (100% pentane as eluent) to afford product 70 (49.0 mg, 71% yield). The structure of the product was confirmed by 1H NMR (500 MHz, CDCl3) and 13C NMR (125 MHz, CDCl3) as follows: 1H NMR δ 5.74-5.64 (m, 1H), 5.13-5.06 (m, 1H), 4.99-4.88 (m, 2H), 2.12 (p, J=7.0 Hz, 1H ), 2.01-1.89 (m, 2H), 1.68 (s, 3H), 1.60 (s, 3H), 1.35-1.26 (m, 2H), 0.99 (d, J=6.9Hz, 3H); 13C NMR δ 144.91, 131.44, 124.80, 112.61, 37.51, 36.89, 25.88, 20.30, 17.83. |