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HETEROCYCLES, Vol. 81, No. 11, 2010
13C-NMR (100 MHz, CDCl3): 13.79, 19.29, 20.67, 20.75, 20.97, 29.79, 31.40, 62.31, 67.63, 69.41,
69.07, 69.14, 101.29, 169.52, 169.86, 170.70. IR (CHCl3): 2959, 2874, 1742, 1433, 1366, 1219, 1117,
1038, 673 cm-1. HRMS: C16H25IO8 (M+ + Na). Cal. 495.0492. Found, 495.0481.
Compound 8; []D28 +1.63 (c 1.06, CHCl3). 1H-NMR (400 MHz, CDCl3): 0.87 (3H, t, J = 6.8 Hz, H-5’),
1. 27-1.30 (4H, m, H-3’, H-4’), 1.53-1.59 (2H, m, H-2’), 2.01 (3H, s, Ac), 2.03 (3H, s, Ac), 2.07 (3H, s,
Ac), 3.42 (1H, dt, J = 9.6, 6.7 Hz, H-1’a), 3.61 (1H, dt, 9.6, 6.7 Hz, H-1’b), 3.97 (1H, ddd, J = 10.0, 4.9,
2.4 Hz, H-5), 4.10 (1H, dd, J = 12.2, 2.4 Hz, H-6a), 4.18 (1H, dd, J = 12.2, 4.9 Hz, H-6b), 4.49 (1H, dd, J
= 4.4, 1.2 Hz, H-2), 4.59 (1H, dd, J = 9.5, 4.4 Hz, H-3), 5.12 (1H, brs, H-1), 5.32 (1H, t, J = 9.8, H-4), IR
(CHCl3): 2928, 2857, 1748, 1456, 1368, 1229, 1120, 1047, 738 cm-1. HRMS: C17H27IO8 (M+ + Na). Cal.
509.0648. Found, 509.0555.
Compound 9; []D28 +16.79 (c 1.02, CHCl3). H-NMR (400 MHz, CDCl3): 0.89 (7H, m, H-6’, H-7’,
1
H-8’), 1.27 (6H, m, H-3’, H-4’, H-5’), 1.55 (2H, m, H-2’), 2.04 (3H, s, Ac), 2.07 (3H, s, Ac), 2.10 (3H, s,
Ac), 3.44 (1H, ddd, J = 13.2, 6.0, 3.0 Hz, H-1a’), 3.64 (1H, ddd, J = 13.2, 6.0, 3.0 Hz, H-1b’), 4.00 (1H,
ddd, J = 9.8, 4.8, 2.4 Hz, H-5), 4.13 (1H, dd, J = 12.1, 2.4 Hz, H-6a), 4.21 (1H, dd, J = 12.1, 4.8 Hz,
H-6b), 4.51 (1H, dd, J = 4.4, 1.1 Hz, H-2), 4.63 (1H, dd, J = 9.8, 4.4 Hz, H-3), 5.15 (1H, brs, H-1), 5.35
(1H, t, J = 9.8 Hz, H-4). 13C-NMR (100 MHz, CDCl3): 14.09, 20.68, 20.76, 20.99, 22.64, 26.07, 29.20,
29.3, 29.34, 29.81, 31.80, 62.29, 67.63, 68.75, 69.06, 69.16, 101.29, 169.54, 169.89, 170.74. IR (CHCl3):
3056, 2929, 1748, 1455, 1423, 1368, 1265, 1229, 1047, 739 cm-1. HRMS: C20H33IO8 (M+ + Na). Cal.
551.1118. Found, 551.0984.
Compound 10; []D28 +1.83 (c 1.01, CHCl3), H-NMR (400 MHz, CDCl3): 1.17 (d, 3H, J = 6.0 Hz,
1
H-2’a), 1.23 (d, 3H, J = 6.0 Hz, H-2’b), 2.05 (s, 3H, Ac), 2.08 (s, 3H, Ac), 2.10 (s, 3H, Ac), 3.80-4.00 (m,
1H, H-1’), 4.08 (ddd, 1H, J = 9.5, 5.0, 2.4 Hz, H-5), 4.14 (dd, 1H, J = 12.0, 2.4 Hz, H-6a), 4.22 (dd, 1H, J
= 12.2, 5.0 Hz, H-6b), 4.48 (d, 1H, J = 4.3 Hz, H-2), 4.66 (dd, 1H, J = 9.5, 4.3 Hz, H-3), 5.26 (brs, 1H,
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H-1), 5.36 (t, 1H, J = 9.7 Hz, H-4). C-NMR (100 MHz, CDCl3): 20.62, 20.68, 20.92, 21.60, 23.03,
30.56, 62.30, 67.75, 69.05, 69.08, 71.06, 99.61, 169.47, 169.77, 170.60. IR (CHCl3): 2972, 2925, 1742,
1433, 1367, 1220, 1113, 1032, 736 cm-1. HRMS: C15H23IO8 (M+ + Na). Cal. 481.0336. Found, 481.0324.
Compound 11; (mixture of diastereomers): []D28 +1.90 (c 1.05, CHCl3), 1H-NMR (400 MHz, CDCl3):
0.77-0.93 (m, 6H, H-4’, isomer A, isomer B), 1.07 (d, 3H, J = 5.0 Hz, H-2’, isomer A), 1.14 (d, 3H, J =
5.3 Hz, H-2’, isomer B), 1.31-1.63 (m, 4H, H-3’, isomer A, isomer B), 1.99 (s, 3H, Ac), 2.01 (s, 3H, Ac),
2.04 (s, 3H, Ac), 3.55-3.68 (m, 2H, H-1’, isomer A, isomer B), 3.98-4.19 (m, 6H, H-5, H-6, isomer A,
isomer B), 4.42 (d, 1H, J = 4.5 Hz, H-2, isomer A), 4.41 (d, 1H, J = 4.5 Hz, H-2, isomer B), 4.53-4.63 (m,
2H, H-3, isomer A, isomer B), 5.19 (brs, 1H, H-1, isomer A), 5.21 (brs, 1H, H-1, isomer B), 5.29 (t, 2H,
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J= 9.7 Hz, H-4, isomer A, isomer B). C-NMR (100 MHz, CDCl3): 9.57, 10.17, 18.59, 20.45, 20.65,