5. Physical properties and spectral data for
1 purified by recrystallization from
petroleum ether (bp
40-60°C) are as follows: mp
72°C; [α]D22 −66.6 (CH
2Cl
2,
c 1.0); IR (CH
2Cl
2) cm
−1: 3600, 3500, 2940, 2860, 1430, 1380, 1280, 1220, 1170, 1100, 1070, 1040, 980, 930, 900, 860, 840;
1H NMR (CDCl
3, 200 MHz) δ: 1.32 (s, 3 H), 1.48 (s, 3 H), 3.02 (d, 1 H, J = 4.9, OH), 3.4-3.6 (m, 4 H), 3.95 (dddd, 1 H, J = 5.2, 5.2, 5.2, 4.9), 4.17 (d, 1 H, J = 10.8), 4.72 (dd, 1 H, J = 6.2, 3.6), 4.82 (dd, 1 H, J = 6.2, 3.6);
13C NMR (CDCl
3, 50 MHz) δ: 9.4, 24.5, 25.9, 69.1, 72.5, 80.0, 81.2, 84.7, 112.4; MS (EI) m/e (rel. intensity): 299 (M −15, 17), 187 (M −127, 3), 171 (15), 144 (30), 127 (3), 86 (26), 69 (59), 59 (51), 57 (51), 55 (23), 44 (24), 43 (100). Anal. Calcd for C
9H
15IO
4: C, 34.41; H, 4.81; I, 40.40. Found: C, 34.55; H, 4.80; I, 40.27.
8. Physical properties and spectral data for
2 are as follows: white solid (mp:
77°C);
[α]D26 −80.5 (CH
3OH,
c 0.502); IR (CH
2Cl
2) cm
−1: 3050, 2960, 2900, 2840, 1600, 1430, 1350, 1200, 1150, 1080, 1060, 1040, 1010, 970, 910, 880, 850;
1H NMR (CDCl
3, 200 MHz) δ: 1.34 (s, 3 H), 1.53 (s, 3 H), 2.66 (dd, 1 H, J = 4.8, 2.7), 2.91 (dd, 1 H, J = 4.8, 4.4), 3.03 (dd, 1 H, J = 6.9, 3.7), 3.29 (ddd, 1 H, J = 6.9, 4.4, 2.7), 3.52 (dd, 1 H, J = 10.8, 3.6), 4.10 (d, 1 H, J = 10.8), 4.70 (dd, 1 H, J = 6.1, 3.7), 4.80 (dd, 1 H, J = 6.1, 3.6);
13C NMR (CDCl
3, 50 MHz) δ: 24.8, 26.0, 43.8, 50.0, 73.2, 81.2, 81.4, 84.6, 112.7; MS (EI) m/e (rel. intensity): 186 (M
+., 0), 171 (M-15, 89), 149 (5), 111 (33), 69 (55), 68 (12), 59 (29), 57 (44), 55 (48), 43 (100), 41 (52), 39 (22), 29 (34). Anal. Calcd for C
9H
14O
4: C, 58.05; H, 7.58. Found: C, 57.83; H, 7.36.