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A solution of ketone SI-04 (3.0 g, 12.1 mmol, 1.0 equiv) in THF (120 mL) was cooled to -78 °C and ethynylmagnesium bromide (0.5 M solution in THF, 121 mL, 60.4 mmol, 5.0 equiv) was added over 20 min. The reaction mixture was stirred at this temperature for 10 min, warmed to -15 °C and stirring was continued for 3 hours. Saturated aqueous NH4Cl (40 mL) was added and the mixture was extracted with EtOAc (3 × 150 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification of the crude product by flash column chromatography (silica gel, hexanes/EtOAc = 10:1 → 5:1) afforded alcohol SI-05 (2.69 g, 81%) as a colorless oil of a 10:1 mixture of inseparable diastereomers. 1H NMR (400 MHz, CDCl3): δ 5.19 (dt, J = 8.0, 6.7 Hz, 1 H), 4.73 (d, J = 5.9 Hz, 2 H), 3.79 (dt, J = 7.0, 4.9 Hz, 1 H), 3.14 (d, J = 5.4 Hz, 1 H), 2.94 (s, 1 H), 2.92 – 2.84 (m, 1 H), 2.66 (s, 1 H), 1.73 – 1.64 (m, 1 H), 1.60 – 1.51 (m, 2 H), 1.31 (dq, J = 12.2, 6.6 Hz, 1 H), 1.17 (d, J = 6.9 Hz, 3 H), 1.08 (d, J = 6.6 Hz, 3 H), 1.04 (s, 3 H), 0.95 (s, 3 H), 0.72 (t, J = 8.7 Hz, 1 H), 0.30 (dd, J = 9.5, 4.8 Hz, 1 H).

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