Multi-step reaction with 16 steps
1: 1.) LDA, HMPA / 1.) hexane, THF, -78 deg C, 30 min, 2.) THF, hexane, from -78 deg C to RT, 15 h
2: 93 percent / Li, NH3, t-BuOH / diethyl ether / 1.5 h / -78 °C
3: 1.) Et3N, 2.) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / 1.) DMF, reflux, 12 h, 2.) benzene, RT, 12 h
4: 1.) O3, pyridine, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, RT, 12 h
5: 87 percent / p-toluenesulfonic acid monohydrate / benzene / 8 h / Ambient temperature
6: 98 percent / palladium acetate, triethyl phosphite / tetrahydrofuran / 20 h / Heating
7: 90 percent / LiAlH4 / tetrahydrofuran / 6 h / -78 °C
8: 73 percent / K2CO3, (NH4)6Mo7O24, tetra-n-butylammonium chloride, aq. H2O2 / tetrahydrofuran
9: 94 percent / NaBH(OAc)3 / tetrahydrofuran / 48 h / Ambient temperature
10: 95 percent / pyridinium p-toluenesulfonate / acetone / 12 h / Ambient temperature
11: 1.) O3, 2.) Me2S / 1.) MeOH, -78 deg C, 2.) MeOH, from -78 deg C to RT, overnight
12: 91 percent / K2CO3 / methanol / 12 h / Heating
13: 100 percent / pyridinium p-toluenesulfonate / methanol / 4 h / Ambient temperature
14: 1.) DBN / 1.) DMF, RT, 1 h, 2.) DMF, RT, 1 h
15: 38 percent / <(CH3)3Si>3SiH, AIBN / toluene / 2 h / 110 °C
16: ethanol / 1 h / 0 °C
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; ammonium heptamolybdate; lithium aluminium tetrahydride; dimethylsulfide; 2,2'-azobis(isobutyronitrile); 2,6-dichloro-benzonitrile; tris-(trimethylsilyl)silane; tetrabutyl-ammonium chloride; ammonia; dihydrogen peroxide; palladium diacetate; pyridinium p-toluenesulfonate; lithium; sodium tris(acetoxy)borohydride; potassium carbonate; toluene-4-sulfonic acid; ozone; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; lithium diisopropyl amide; triethyl phosphite;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; acetone; toluene; benzene;
