IIIa
| 3400 cm−1 (—OH), 1690 and 1610 cm−1 (conjugated carbonyl) | 4.92 (d, 1H, J = 6.0 Hz, H—4), 2.27 (s, 3H, H—9), 2.03 (s, 3H, H—10), 1.79 (2d, 2H, J = 2.1 Hz, H—3), 1.19 and 1.02 (2s, 6H, H—6 and H—7) | m/z: 168 (M+), 153 (M+—CH3), 150 (M+—H2O), 135 (M+—CH3—H2O, bp), 107 (M+—CO—CH3—H2O) HRMS: C10H16O2 requires 168.1150, found 168.1147 |
IIIb
| 3400 cm−1 (—OH), 1690 and 1610 cm−1 (conjugated carbonyl) | 4.26 (s, 2H, H—9), 2.4 (t, 2H, J = 7.2 Hz, H—4), 1.87 (s, 3H, H—10), 1.7 (t, 2H, J = 7.5 Hz, H—3), 1.02 (s, 6H, H—6 and H—7) | m/z: 168 (M+), 153 (M+—CH3), 150 (M+—H2O), 135 (M+—CH3—H2O, bp), 107 (M+—CO—CH3—H2O) HRMS: C10H16O2 requires 168.1150, found 168.1157 |
IIIc
| 3400 cm−1 (—OH), 1690 and 1613 cm−1 (conjugated carbonyl) | 4.15 (s, 2H, H—10), 2.46 (m, 2H, H—4), 2.22 (bs, 3H, H—9), 1.68 (t, 2H, J = 7.8 Hz, H—3), 0.97 (s, 6H, H—6 and H—7) | m/z: 168 (M+), 153 (M+—CH3), 150 (M+—H2O), 135 (M+—CH3—H2O, bp) 125 (M+—CO—CH3), 107 (M+—CO—H2O—CH3) HRMS: C10H16O2 requires 168.1150, found 168.1153 |
IVa
| 3400 cm−1 (—OH), 1690 and 1605 cm−1 (conjugated carbonyl) | 2.71 (m, 2H, H—8), 2.49 (m, 2H, H—3), 2.18 (q, 2H, J = 6.1 Hz, H—10), 1.95 (m, 2H, H—4), 1.23 (s, 3H, H—6), 1.07 (t, 3H, J = 6.2 Hz, H—9), 1.04 (t, 3H, J = 6.04 Hz, H—11) | m/z: 182 (M+), 164 (M+—H2O), 149 (M+—CH3—H2O, bp), 121 (M+—CO—CH3—H2O) HRMS: C11H18O2 requires 182.1307, found 182.1302 |
Va
| 3412 cm−1 (—OH), 1678 and 1610 cm−1 (conjugated carbonyl) | 2.04–2.57 (m, 10H, methylene protons), 1.33 (s, 3H, H—7), 1.03 (q, 6H, J = 7.5 Hz, H—10 and H—12) | m/z: 192 (M+), 178 (M+—H2O), 163 (M+—CH3—H2O), 135 (M+—CO—CH3—H2O) HRMS: C12H20O2 requires 196.1463, found 196.11462 |
Vb
| 1655 and 1610 cm−1 (conjugated carbonyl) | 5.88 (bs, 1H, H—2), 2.63 (t, 2H, J = 6.3 Hz, H—4), 2.42 (q, 2H, J = 7.5 Hz, H—9), 2.29 (t, 2H, J = 6.6 Hz, H—5), 2.17 (q, 2H, J = 7.5 Hz, H—11), 1.93 (s, 3H, H—7), 1.07 (t, 3H, J = 7.5 Hz, H—10), 1.03 (t, 3H, J = 7.5 Hz, H—12) | m/z: 178 (M+), 163 (M+—CH3), 149 (M+—C2H5), 96 (M+—C5H6O), 82 (M+—C7H12) HRMS: C12H18O requires 178.1357, found 178.1343 |