Multi-step reaction with 20 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 10 h / Ambient temperature
2: 96 percent / NBS / CHCl3 / 45 °C
3: 90 percent / PDC / CHCl3
4: 85 percent / NaClO2 / dimethylsulfoxide / 12 h / Ambient temperature
5: SOCl2 / Heating
6: Et3N, DMAP / CHCl3 / 0 °C
7: 25 percent / NaOAc / Pd(PPh3)2Cl2 / N,N-dimethyl-acetamide / 130 °C
8: 68 percent / LiAlH4 / tetrahydrofuran / Ambient temperature
9: 90 percent / K2CO3 / acetone / 3 h / Ambient temperature
10: 80 percent / NaH / tetrahydrofuran / 20 h / Ambient temperature
11: p-TsOH / methanol / 6 h / 60 °C
12: Et3N, DMAP / CHCl3 / Ambient temperature
13: K2CO3 / methanol / 0.17 h
14: PDC / dimethylformamide / 10 h / Ambient temperature
15: diethyl ether; methanol
16: 80 percent / H2 / Pd/C (10percent)
17: 86 percent / PDC / CHCl3
19: methanol; CHCl3
20: 65 percent / HCl
With
hydrogenchloride; dmap; sodium chlorite; N-Bromosuccinimide; lithium aluminium tetrahydride; dipyridinium dichromate; thionyl chloride; hydrogen; sodium acetate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine;
bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; chloroform; N,N-dimethyl acetamide; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1016/0040-4039(92)88096-N