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10
Preparation of
(-)-3. To a stirred solution of karahana lactone (-)-2
[6]
(400
mg, 2.41 mmol) in dry CH2Cl2 (40 mL) was added
selenium dioxide (107 mg, 0.96 mmol), tert-butyl hydroperoxide
(70 wt% in water, 868 mg, 9.64 mmol) and a catalytic amount
of salicylic acid under an argon atmosphere. The reaction mixture
was heated to reflux for 3 d, cooled to r.t. and Na2SO3 (2.5
g, 20 mmol) and 1 mL of water were added. The mixture was stirred
for a further 30 min, filtered through a pad of MgSO4 and
concentrated. After purification by crystallization from Et2O-hexane,
354 mg of pure alcohol (-)-3 were
obtained as white crystals (rdt 85%).
11 Spectroscopic data of compounds (-)-3 and (-)-1:
(-)-3: mp 155 °C, [α]D
25 -142.9
(c 1.0, CHCl3). IR (KBr):
3440, 3091, 1759, 1036, 905 cm-1. 1H
NMR (500 MHz, CDCl3): δ = 5.18 (s,
1 H, H-9), 5.08 (s, 1 H, H-9), 4.42 (d, J = 6.1
Hz, 1 H, H-3), 4.36 (br. d, J = 3.7
Hz, 1 H, H-5), 2.77 (s, 1 H, H-1), 2.22 (dd, J = 15.7,
3.8 Hz, 1 H, Hα-4), 2.08 (ddd, J = 15.7,
6.1, 1.5 Hz, 1 H, Hβ-4), 1.21 (s, 3 H, CH3
β),
0.95 (s, 3 H, CH3
α).
13C
NMR (125 MHz, CDCl3): δ = 176.6 (C-7),
143.9 (C-2), 117.0 (CH2-9), 84.3 (CH-5), 68.0 (CH-3),
56.6 (CH-1), 42.8 (C-8), 32.6 (CH2-4), 25.3 (CH3
),
20.1 (CH3
). Anal. Calcd for C10H14O3:
C, 65.92; H, 7.74. Found: C, 65.64; H 7.72.
(-)-1: Mp 59 °C, [α]D
25 -39.0
(c 1.0, CHCl3). IR (KBr): 1661,
1630, 1254, 1104 cm-1. 1H
NMR (200 MHz, CDCl3): δ = 5.37 (s,
1 H, H-7), 4.26 (t, J = 4.8
Hz, 1 H, H-5), 4.12-4.05 (m, 2 H, Hdioxolane),
3.94-3.87 (m, 2 H, Hdioxolane), 2.76 and 2.60
(ABX, J = 13.7,
5.8, 4.4 Hz, 2 H, H-6), 1.92 (s,
3 H, H-8), 1.30 (s, 3
H, CH3) 1.22 (s, 3 H, CH3), 0.85 (s, 9 H, (CH3)3C-),
0.06 (s, 3 H, CH3-Si), 0.05 (s, 3 H, CH3-Si).
13C
NMR (50 MHz, CDCl3): δ = 212.2 (C-1),
139.1 (C=), 133.0 (C=), 102.0 (CH-7), 72.2 (CH-5),
64.7 (CH2dioxolane), 64.4 (CH2dioxolane),
47.1 (C-2), 45.6 (CH2-6), 25.6 (CH3)3C-), 24.6
(CH3), 23.8 (CH3), 17.9 (CH3)3C-),
17.2 (CH3-8), -4.6 (CH3-Si), -4.8
(CH3-Si). Anal. Calcd for C18H32O4Si:
C, 63.49; H, 9.47. Found: C, 63.67; H 9.45.