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Dissolve (-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (28.85 g, 135 mmol, prepared in example 10) in ethanol (75 mL) and treated with Raney nickel (1.85 g, 32 mmol, previously washed with water (2×50 mL) and ethanol (2×50 mL)). Charge the atmosphere with hydrogen at 50 psi (344.74 kPa) and shake the mixture. After 5.25 hours, filter the reaction. Cool the filtrate to 0° C. and treat with sodium borohydride (0.54 g, 14.3 mmol). After stirring for 2 hours, concentrate the solution under vacuum and distill the resulting oil by Kugelrohr distillation (40°-60° C., 1 mmHg) to provide the title compound (25.5 g, 87%) as a colorless oil, [α]20 =-3.9°, (c=0.99, chloroform); 1H NMR (CDCl3) δ4.4 (m, 1H), 4.3 (m, 1H), 3.03 (d, 1H, J=10.5 Hz), 1.9-1.6 (m, 6H), 0.89 (s, 9H), 0.07 (s, 6H); 13C NMR (CDCl3) δ74.9, 74.1, 44.4, 34.2, 34.1, 25.8, 17.9, -4.9, -5.0; IR (neat) νmax 3405, 2957, 2932, 2888, 2858, 1256, 1091, 1069, 1038, 1026 cm-1 ; CIMS m/e (% relative intensity) 217 (M+H+ 81), 199 (M+H+ --H2O, 37) 67 (100). This (-)-enantiomer (title compound) could not be separated from the (+)-enantiomer (antipode) using the previously described chiral column.

1. washpreviously washed with water (2×50 mL) and ethanol (2×50 mL))
2. additionCharge the atmosphere with hydrogen at 50 psi (344.74 kPa) and shake the mixture
3. filtrationfilter
4. customthe reaction
5. concentrationconcentrate the solution under vacuum
6. distillationdistill the resulting oil
7. distillationby Kugelrohr distillation (40°-60° C., 1 mmHg)