2406
J. Org. Chem. 1988, 53, 2406-2409
7.5 Hz), 2.12 (1 H, m, H-3), 2.05 (3 H, s, OAc-Me), 1.64 (4 H, m), 1.40 (3 H, s, (2-15 Me), 1.33 (3 H, d, J = 7.1 Hz, C-18 Me), 1.31 (2 H, m), 0.90 (3 H, d, J = 6.9 Hz, C-20Me), 0.89 (3 H, t, J = 7.0 Hz). Compound 8 showed the following spectral characteristics: UV (MeOH) A, 237 nm (t 6400); IR (CH2C12)3580,3050, 1780,1730,1370,1240,1170,1015,1000,910cm-'; CIMS (NH,), m / z (relative intensity) 503.5 (100) for CBHa08; HRMS (30 eV), m/z (relative intensity) 476.2810 (M+- CO, CnH,07, ll),434.2681 (3), 360.1951 (CzlHz805, 16), 176.0874 (CllH1202, 23), 166.0997 (ClOHl4O2, 71), 124.0892 (81), 99.0812 (100); 'H NMR (360 MHz, CDC13, 51 "C) 6 6.26 (1 H, d, J = 16.4 Hz, H-6), 5.76 (1H, d, J = 16.4 Hz, H-7), 5.08 (1H, dd, J = 7.6, 4.6 Hz, H-2), 5.00 (1 H, bs, H-16), 4.94 (1 H, bs, H-16), 4.87 (1H, br t, J = 3.8 Hz, H-121, 4.26 (1 H, bs, H-9), 3.34 (1 H, t, J = 3.8 Hz, H-13), 2.81 (1H, d, J = 3.8 Hz, H-14), 2.81 (1H, q, J = 7.1 Hz, H-17), 2.32 (2 H, t , J = 7.3 Hz), 2.25 (1 H, m, H-3), 2.10 (3 H, s, OAc-Me), 1.95 (1 H, m, H-11), 1.84 (1H, m, H-3), 1.63 (4 H, m), 1.32 (2 H, m), 1.31 (3 H, s, C-15 Me), 1.20 (3 H, d, J = 7.1 Hz, C-18 Me), 1.08 (3 H, d, J = 7.3 Hz, C-20 Me), 0.90 (3 H, t, J = 6.8 Hz). Product 9 showed the following spectral properties: UV (MeOH) A,, 230 nm (e 10500); IR (CH2C1,) 3680,3450-3400 br, 3050,1780,1735, 1370,1185,1070,1035,1000,905 cm-l; CIMS (NHJ, m / z (relative intensity), 424.2 (M + NH4+,54), 406.5 (
