HCID 57814787, compound → HCID 57814803, compound

Participants

Reaction Steps

A solution of enone 13 (425 mg, 0.67 mmol) in 7 mL of dichloromethane was cooled to −30° C. and stirred rapidly while solid (R)-methylCBS-borane complex (350 mg, 1.20 mmol) was added in one portion. The resulting solution was stirred at −30° to −20° C. for 1 h. TLC analysis at this stage showed no starting material left and the reaction mixture was quenched with 2 mL of methanol, the cooling bath was removed and the mixture was stirred at 25° C. 60 min. The mixture was concentrated in vacuo to remove solvents and the residual products were purified by FCC on silica gel (40 g Silicycle cartridge, 500 mL of 10% EA-hexanes, then 500 mL of 20% EA-hexanes) to yield 316 mg (74% yield) of (15S)-alcohol 14; 1H NMR (CDCl3): 0.04 (s, 6H), 0.87 (s, 9H), 0.93 (t, J=6 Hz, 3H), 1.10 (d, J=4.8 Hz, 3H), 1.24-1.88 (m, 24H), 2.10-2.32 (m, 4H), 3.45 (m, 1H), 3.80 (m, 2H), 4.03 (m, 4H), 4.61 (dt, J=2.4, 14.4 Hz, 1H), 5.56 (m, 2H).

Provenance & Evidence