HCID 10622632, compound → HCID 10527471, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 824 mg (1.90 mmol) of 5 in 120 mL of acetone was cooled to 0° C. and 710 μL of Jones reagent solution (8 M solution of CrO3 in aqueous H2SO4)37 was added. The reaction mixture was stirred at 0° C. for 30 min, diluted with MeOH (20 mL) and H2O (20 mL), concentrated to about 30 mL, and extracted with CH2Cl2 (3×, 70 mL). Combined organic extracts were dried over Na2SO4 and concentrated in vacuo. Purification of the residue by flash chromatography on a 2×17 cm column of silica gel using EtOH/CH2Cl2 (5:95) gave 784.4 mg (92%) of 6 as a white foam. Data for 6: TLC, T-4, Rf0.78. 1H NMR (500 MHz, CDCl3) δ 0.87 (s, 3H, H-18), 2.10 (s, 3H, OAc), 5.02 (d, 1H, J=7.1 Hz, H-17α), 5.04(s, 2H, benzylic), 6.72 (d, 1H, J=2.8 Hz, H-4), 6.79 (dd, 1H, J=8.5, 2.8 Hz, H-2), 7.20 (d, 1H, J=8.5 Hz, H-1), 7.31-7.44 (m, 5H, Ar—H); HRMS (ES) calcd for C28H32O5Na (M+Na+) m/e 471.2147, found m/e 471.2146.

Provenance & Evidence