Multi-step reaction with 14 steps
1: 100 percent / tetrahydrofuran / 24 h / 30 °C
2: Et3N / 1 h / -78 - 0 °C
3: DMAP / 24 h / Ambient temperature
4: H2 / 10percent Pd/C / 24 h / Ambient temperature
5: Et3N / 1 h / -78 - 0 °C
6: 48 h / -25 °C
7: Me3SiOSO2CF3 / 48 h / -20 °C
8: tetrahydrofuran / 18 h / 30 °C
9: 88 percent / LiTMP, DMPU / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 to -10 deg C, 60 h
10: aq. KOH / H2O / 32 h / 80 °C
11: 0.5 h / Ambient temperature
12: NH3
13: Pb(OAc)4 / dimethylformamide / 15 h / 100 °C
14: TsOH / acetone; H2O / 2.5 h / Heating
With
lead(IV) acetate; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; 2,2,6,6-tetramethylpiperidinyl-lithium; ammonia; hydrogen; toluene-4-sulfonic acid; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; water; N,N-dimethyl-formamide; acetone;
DOI:10.1039/a703387g