Reaction Steps
By using the general procedure above, (−)-thujone (0.186 g, 1.22 mmol) was reacted with 1,10-phenanthroline to provide 0.083 g (45% yield) of the title compound as a colorless oil: 1H NMR (300 MHz, CDCl3) δ9.16 (dd, J=4.50, 1.80 Hz, Hp9), 8.27 (d, J=8.40 Hz, Hp4), 8.24 (dd, J=8.10, 1.80 Hz, Hp7) 7.82 and 7.76 (two d, J=8.80 Hz, Hp5 and Hp6), 7.72 (d, J=8.40 Hz, Hp3), 7.62 (dd, J=8.10, 4.50 Hz, Hp8), 6.38 (br s, OH), 2.75 (dq, J=6.6, 4.5 Hz, CHCH3), 2.50 (dd, J=13.5, 1.2 Hz, C(OH)CHH), 2.21 (d, J=13.5 Hz, C(OH)CHH), 1.53 (sep, 6.9 Hz, CH(CH3)2), 1.37 (t, J=3.9 Hz, cyclopropyl H), 1.31 (dd, J=4.2, 8.4 Hz, cyclopropyl H), 1.07 (d, J=6.9 Hz, CH3), 0.95 (d, J=6.9 Hz, CH3), 0.89 (d, J=6.9 Hz, CH3), 0.37 (dd, J=4.5, 9.0 Hz, cyclopropyl H); 13C NMR (75 MHz) δ165.09, 150.16, 145.56, 142.86, 137.10, 136.05, 128.98, 127.17, 126.29, 126.05, 122.87, 119.72, 81.85, 48.66, 46.71, 33.01, 32.70, 29.53, 20.10, 19.94, 13.12, 11.60; IR (CHCl3) 3381 (OH), 2957 (C—H Ar), 2928 (CH), 850 (C—H Ar) cm−1; HRMS m/e Calcd for C22H25N2O (MH+): 333.1967, found: 333.1943.
