HCID 131725388, compound → HCID 69640538, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 15.8 mg (0.0269 mmol) of 58 in anhydrous THF (500 μL) was stirred at rt as 108 μL of a 1 M solution of LiEt3BH in THF (0.108 mmol) was added and the reaction was stirred and heated at 65° C. for 5 h then quenched at rt with EtOH (1 mL). To the reaction mixture was added diglyme (2 mL), 48 mg (0.431 mmol) Et3NO and the reaction was stirred and heated at 150° C. for 1 h allowing the THF to evaporate. The reaction mixture was allowed to cool to rt, poured into H2O (50 mL) and extracted with EtOAc (3×, 50 mL). Combined organic extracts were washed with 10% Na2S2O5 (30 mL), H2O (30 mL), dried over Na2SO4 and concentrated in vacuo giving a colorless oil. Purification by flash chromatography on a 2×17 cm column of silica gel using 4:1 hexanes/EtOAc as eluent gave 9 mg (97%) of 59. Data for 59: TLC, T-1, Rf 0.73; 1H NMR (400 MHz, CDCl3) δ 0.86 (s, 3H, H-18), 0.90 (t, 1H, J=10.2 Hz, H-14), 1.12 (d, 3H, J=6.2 Hz, 15α-CH3), 3.38 (s, 3H, CH2OCH3), 3.64 (t, 1H, J=8.6 Hz, H-17α), 3.79 (s, 3H, ArOCH3), 4.65–4.67 (AB quartet, 2H, JAB=6.6 Hz, OCH2O), 6.62 (d, 1H, J=2.8 Hz, H-4), 6.72 (dd, 1H, J=8.6, 2.8 Hz, H-2), 7.22 (d, 1H, J=8.6 Hz, H-1).

Provenance & Evidence