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16
General Experimental
Procedure. To a well-stirred solution of (E)-2-(4-bromobut-2-enyl)-(2-prop-2-ynyl)-malonic
acid dimethyl ester 4f (451 mg, 1.5 mmol)
in dry THF (1 mL) and distilled water (1 mL) at room temperature, was
added indium powder (Aldrich, 99.99%, 171 mg, 1.5 mmol,
1 equiv). The mixture was stirred for a further 18 hours and then
the reaction mixture was poured onto a mixture of Et2O
and dilute HCl (5% v/v). The aqueous layer was
extracted with Et2O (2 × 25 mL) and the combined organic
layers were washed with water (2 × 25 mL), saturated aqueous
NaCl (1 × 25 mL) and dried (MgSO4). Filtration
and removal of solvent gave a residue which was purified by chromatography
(SiO2, hexane/EtOAc, 5:1) to give the cyclised
product 5f (249 mg, 74%) as a
clear colourless oil (Rf = 0.52). 1H
NMR (360.13 MHz, CDCl3)
δH = 2.01
(1 H, dd, J = 11 Hz, 13 Hz),
2.57 (1 H, dd, J = 8 Hz, 13
Hz), 2.95 (1 H, ddd, J = 3 Hz,
6 Hz, 18 Hz), 3.08 (1 H, br d, J = 18
Hz), 3.17 (1 H, m), 3.82 (1 H, s with allylic coupling), 4.98 (1
H, s with allylic coupling), 5.05 (1 H, br s), 5.08 (1 H, m), 5.64
(1 H, ddd, J = 8 Hz, 10.5 Hz,
13 Hz) ppm. 13C NMR (100.62 MHz, CDCl3) δC = 40.70,
48.08, 53.20, 53.26, 58.91, 108.55, 116.51, 139.44, 150.76, 172.40, 172.59
ppm. IR (thin film): 3660, 3471, 3078, 2953, 1731, 1714, 1659, 1642,
1453, 1433, 1267, 1199, 1167, 1072, 917, 891, 821, 766, 718, 690,
666 cm-1. MS (FAB): m/z (%) = 225 (73.2) [MH+],
193 (36.5), 165 (65.1), 154 (74.3), 137 (68.1), 136 (61.7), 105
(100), 91 (49.7), 77 (49.1).
17 All compounds described gave 1H, 13C,
IR and MS data consistent with the structures reported.
