References
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- General Experimental Procedures. Mps: uncorr, NMR spectra were recorded on a Bruker AM-400 and DRX-500 instruments with TMS as internal standard. 1H-NMR, 1H-1H COSY and ROESY spectra were recorded at 400.13 and 500.13 MHz; 13C-NMR and DEPT spectra were recorded at 100.6 and 125.8 MHz. 13C-NMR assignments were determined by HMQC and HMBC spectra; EI-MS and HREI-MS data were carried out on a VG Autospec 3000 mass spectrometer at 70 eV.
- Properties of Integrifolin (1): C30H48O3 (HREIMS found 456.3601, Calc. 456.3603); colorless granular crystals (MeOH), m. p. 315.5-316.5 [ddot]C; [α]D 18 -21.6[ddot] (C5H5N, c = 0.232); IR vmax KBr: 3360, 3233, 2956, 2872, 168. (s), 1471, 1448, 1406, 1370 cm−1; EI-MS m/z (rel. int.) 456 [M]+(62), 441 [M-CH3]+(100), 423 [M-CH3H2O]+(35), 394 [M-CH3-H2O-CHO]+ (24), 379 [M-CH3-H2O-COOH]+(40), 303 (13), 289 (94), 271 (34), 243 (17), 227 (35), 205 (20), 191 (19), 173 (21), 159 (26), 137 (53), 119 (53), 105 (57), 95 (80), 81 (59), 69 (65), 55 (84); 1H-NMR (C5D5N) δ: 1.48 (1H, overlapped, H-1α), 2.08 (1H, overlapped, H-1β), 2.01 (1H, m, H-2α), 2.72 (1H, overlapped, H-2β), 3.48 (1H, dd, J = 12.1, 4.2 Hz, H-3α), 1.71 (1H, overlapped, H-5α), 1.78 (1H, overlapped, H-6α), 1.53 (1H, overlapped, H-6α), 2.72 (1H, overlapped, H-7α), 2.08 (1H, overlapped, H-7β), 2.15 (1H, d-like, J = 12.2 Hz, H-8α), 5.44 (1H, dd, J = 5.3, 2.7 Hz, H-11), 1.53 (2H, overlapped, H2-12), 1.49 (1H, overlapped, H-11α), 1.32 (1H, overlapped, H-15β), 1.34 (1H, overlapped, H-16α), 1.64 (1H, overlapped, H-16β), 1.50 (1H, overlapped, H-18α), 1.29-1.41 (2H, overlapped, H2-19), 1.78 (1H, m, H-20α), 1.18 (1H, m, H-20β), 0.89 (1H, m, H-21β), 1.75 (3H, s, Me-22), 1.36 (3H, s, Me-24), 0.92 (3H, s, Me-25), 0.81 (3H, s, Me-26), 0.78 (3H, s, Me-27), 1.43 (1H, overlapped, H-28), 0.85 (3H, d, J = 6.5 Hz, Me-29), 0.91 (3H, d, J = 6.5 Hz, Me-30); 13C-NMR (C5D5N): 41.0 (C-1), 30.2 (C-2), 78.6 (C-3), 50.7 (C-4), 46.8 (C-5), 18.9 (C-6), 20.5 (C-7), 40.1 (C-8), 150.8 (C-9), 37.1 (C-10), 117.3 (C-11), 37.1 (C-12), 38.1 (C-13), 38.9 (C-14), 29.6 (C-15), 36.6 (C-16), 43.3 (C-17), 52.3 (C-18), 20.5 (C-19), 28.6 (C-20), 59.8 (C-21), 24.8 (C-22), 179.9 (C-23), 24.1 (C-24), 16.1 (C-25), 15.9 (C-26), 14.3 (C-27), 31.1 (C-28), 22.4 (C-29), 23.3 (C-30).
- X-ray Crystallographic Analysis of 1: A single crystal of C30H48O3 having approximate dimensions of 0.50 × 0.60 × 0.70 mm3 was used for intensity data collection on a MAC Science DIP-2030K diffractometer with graphite monochromatized Mo-Kα radiation (γ = 0.71073 Å). The distance between the crystal and image plate is 100mm, and a total of 2622 unique reflections were obtained using ω scan from 0-180°. The crystal belongs to orthorhombic, with a = 10.427 (1) Å, b = 13.424 (1) Å, c = 19.063 (1) Å, V = 2668.3 (4) Å3. For Z = 4 and F. W. = 456.70, the calculated density is 1.137 g/cm3. The space group was determined to be P212121. The structure was solved by direct methods (SHELX-86) and expanded using Fourier techniques (DIRDIF94). The block-diagonal matrix least-square refinement for all of nonhydrogen atoms gave the final Rf = 0.058 and Rw = 0.056 (W= 1/σ2|F|). The maximum and minimum peaks on the final difference Fourier map corresponded to 0.240 and -0.170 e−/Å3, respectively.