Compound A9

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InChIKey YATKMKYCBKTEJF-QFLXWJJHSA-N

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Phenyllithium (3.75 mL of a 1.8 M solution in dibutyl ether, 6.76 mmol) was slowly added to a stirring solution of A14 (877 mg, 2.25 mmol) in anhydrous toluene at room temperature. The reaction continued to stir for an additional two hours before being cooled to 0 °C and slowly quenched with a saturated solution of ammonium chloride. The contents of the reaction were then transferred to a separatory funnel and extracted with dichloromethane (3x). The organic layers were then combined, dried with magnesium sulfate and concentrated under reduced pressure to give a crude white foam. This reaction does not go to completion and has been previously described.32 The desired alcohol A9 and starting ketone A14 are readily separated via column chromatography using 7:1 to 2:1 hexanes/ethyl acetate to give 514 mg of alcohol A9 (49% yield) as a white foam and 229 mg of ketone A14 (26% recovery). M.p. 181-182 °C. 1H NMR (CDCl3, 500 MHz, 50 °C): δ 7.46 (m, 2H), 7.30 - 7.22 (m, 2H), 7.15 (td, J = 7.2, 1.3 Hz, 1H), 5.29 (dt, J = 4.6, 2.1 Hz, 1H), 3.86 - 3.64 (m, 8H), 2.51 (dq, J = 14.8, 3.0 Hz, 1H), 2.23 (d, J = 14.5 Hz, 1H), 2.18 (m, 1H), 2.14 - 1.96 (m, 4H), 1.93 - 1.76 (m, 3H), 1.68 (td, J = 11.5, 6.1 Hz, 1H), 1.57 (s, 1H), 1.50 (td, J = 14.0, 4.5 Hz, 1H), 1.44 - 1.17 (m, 2H), 1.34 (s, 3H buried in multiplet), 1.26 - 1.17 (m, 1H) 1.20 (s, 3H buried in multiplet) 0.98 (dt, J = 13.6, 3.8 Hz, 1H), 0.67 (td, J = 13.9, 4.1 Hz, 1H). 13C NMR (CDCl3, 125 MHz, 50 °C): δ 153.0, 141.9, 128.0, 126.0, 125.2, 121.2, 119.8, 109.0, 79.8, 65.2, 64.7, 64.5, 64.2, 57.2, 52.9, 51.7, 45.3, 41.7, 40.7, 37.9, 34.5, 32.9, 31.5, 31.2, 23.7, 22.2, 16.3. HRMS(ESI): m/z calc. for C29H39O5 [M+H]+: 467.2797, found: 467.2790.