Multi-step reaction with 22 steps
1: CH2Cl2; hexane / 17 h / Ambient temperature
2: 1.18 g / NEt3, DMAP / CH2Cl2 / 17 h / Ambient temperature
3: 93 percent / p-toluenesulfonic acid monohydrate / acetone / 36 h / Ambient temperature
4: 87 percent / H2 / Pd-C / ethanol / 24 h / 760 Torr / Ambient temperature
5: 1) (COCl)2, DMSO, 2) NEt3 / 1) CH2Cl2, -78 deg C, 15 min, 2) CH2Cl2, 0 deg C, 20 min
6: 88 percent / BuLi / tetrahydrofuran; CH2Cl2 / 1 h / -78 °C
7: 98 percent / H2 / Lindlar catalyst / methanol / 48 h / 760 Torr / Ambient temperature
8: 100 percent / DMAP, NEt3 / CH2Cl2 / 15 h / Ambient temperature
9: 63 percent / DDQ / CH2Cl2; H2O / 0.5 h / 0 °C
10: 90 percent / pyridinium dichromate, 4 Angstroem molecular sieves / CH2Cl2 / 2 h / Ambient temperature
11: NaClO2, NaH2PO4*2H2O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 1.5 h / 0 °C
12: 34.0 mg / KOH / methanol; H2O / 24 h / Ambient temperature
13: 1) 2,4,6-trichlorobenzoyl chloride, NEt3, 2) DMAP / 1) toluene, room temperature, 18 h, 2) toluene, room temperature, 1 h
15: 92 percent / LiAlH4 / diethyl ether / 1.5 h / 0 - 20 °C
16: 95 percent / KH, TBAI / tetrahydrofuran / 2 h / Heating
17: 75 percent / 1 M aq. HCl / methanol / 3 h / Ambient temperature
18: 71 percent / NEt3, DMAP / CH2Cl2 / 26 h / Ambient temperature
19: 100 percent / K2CO3 / methanol / 2.5 h / Ambient temperature
20: 76 percent / dimethylsulfoxide / 4 h / Ambient temperature
21: 95 percent / H2 / Lindlar catalyst / benzene / 0.5 h / 760 Torr / Ambient temperature
22: 1) (COCl)2, DMSO, 2) NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) CH2Cl2, 0 deg C, 30 min
With
hydrogenchloride; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium on activated charcoal; Lindlar's catalyst;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4020(97)10253-8