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10. All new compounds were fully characterized by IR, 1H
NMR (NOE effect) and 13C NMR. Selected analytical
1
data: 8. IR (film): 3439, 3093, 1759, 1646, 1035 cm−1. H
NMR (200 MHz, CDCl3): l 5.78 (dd, 1H, J=17.6, 11.1
Hz, C9ꢁH), 5.23 (dd, 1H, J=11.1, 0.9 Hz, C10ꢁHcis), 5.23
(s, 1H, CꢁHmethylene), 5.15 (dd, 1H, J=17.6, 0.9 Hz,
C10ꢁHtrans), 5.10 (s, 1H, CꢁHmethylene), 4.43–4.36 (m, 2H,
C5ꢁH and C7ꢁH), 2.91 (s, 1H, C3ꢁH), 2.18 (t, 2H, J=3.2
Hz, C6ꢁH), 1.30 (s, 3H, CH3). 13C NMR (50 MHz,
CDCl3): l 176.1 (CO), 143.3 (C), 137.2 (CH), 118.0
(CH2), 117.9 (CH2), 84.1 (CH), 67.9 (CH), 56.3 (CH),
47.9 (C), 32.6 (CH2), 22.6 (CH3). Anal. calcd for
C11H14O3: C, 68.02; H, 7.27. Found: C, 68.21; H, 7.25.
10. IR (film): 3428, 3081, 1754, 1637, 1048 cm−1 1H
.
NMR (300 MHz, CDCl3): l 5.92 (dd, 1H, J=17.5, 10.9
Hz, C9ꢁH), 5.36 (d, 1H, J=2.6 Hz, CꢁHmethylene), 5.28 (d,
1H, J=11.1 Hz, C10ꢁHcis), 5.18 (d, 1H, J=17.6 Hz,
C10ꢁHtrans), 5.05 (d, 1H, J=2.6 Hz, CꢁHmethylene), 4.44–
4.37 (m, 2H, C5ꢁH and C7ꢁH), 3.02 (s, 1H, C3ꢁH), 2.49
(ddd, 1H, J=13.6, 7.8, 4.4 Hz, C6ꢁHe), 1.84 (dd, 1H,
J=13.6, 9.8 Hz, C6ꢁHa), 1.28 (s, 3H, CH3). 13C NMR (75
MHz, CDCl3): l 176.1 (CO), 141.9 (C), 137.3 (CH), 117.8
(CH2), 112.4 (CH2), 85.4 (CH), 65.7 (CH), 58.3 (CH),
47.7 (C), 34.6 (CH2), 21.6 (CH3). Anal. calcd for
C11H14O3: C, 68.02; H, 7.27. Found: C, 68.32; H, 7.24.
1
1 IR (film): 3458, 3100, 1766, 1105 cm−1. H NMR (200
MHz, CDCl3): l 6.11 (dd, 1H, J=17.5, 11.1 Hz, C9ꢁH),
5.36 (dd, 1H, J=11.1, 0.6 Hz, C10ꢁHcis), 5.26 (dd, 1H,
J=17.5, 0.6 Hz, C10ꢁHtrans), 4.43 (de´largi, 1H, J=4.4 Hz,
C7ꢁH), 4.24 (dd, 1H, J=10.1, 7.8 Hz, C5ꢁH), 3.35 and
2.67 (AB, 2H, J=4.8 Hz, C20ꢁH), 2.60 (ddd, 1H, J=14.2,
7.8, 4.4 Hz, C6ꢁHe), 2.07 (d, 1H, J=1.4 Hz, C3ꢁH), 1.99
(ddd, 1H, J=14.2, 10.3, 1.0 Hz, C6ꢁHa), 1.31 (s, 3H,
CH3). 13C NMR (50 MHz, CDCl3): l 174.8 (CO), 136.0
(CH), 118.7 (CH2), 84.5 (CH), 64.0 (CH), 59.8 (C), 55.5