Multi-step reaction with 24 steps
1: 86 percent / Amberlyst-15 / benzene / 12 h / Heating
2: 1.) NaH, 2.) DMAP / 1.) THF, 0 deg C, 2.) THF, 0 deg C to room temp., 20 h
3: 70 percent / K2CO3, CuO / dimethylformamide / 1.5 h / Heating
4: 58 percent / TMEDA, sec-BuLi / tetrahydrofuran; cyclohexane / -78 deg C to room temp., then overnight
5: 86 percent / imidazole / CH2Cl2 / 0.5 h / Ambient temperature
6: 1.) TMEDA, sec-BuLi / 1.) THF, cyclohexane, -78 deg C, 1 h; 2.) THF, cyclohexane, -78 deg C to room temp., overnight
7: 92 percent / diethyl ether / -78 °C
8: 1.) Et3N, methanesulfonyl chloride, 2.) DBU / 1.) CH2Cl2, 2.) CH2Cl2, 24 h
9: 96 percent / CHCl3 / 12 h / Heating
10: 72 percent / AIBN, Bu3SnH / toluene / 3 h / Heating
11: 79 percent / Bu4N(1+)F(1-) / tetrahydrofuran / 0.08 h
12: 1.) (Bu3Sn)2O, 3-Angstroem molecular sieves, 2.) I2 / 1.) toluene, 2 h, 2.) toluene, THF, room temp., 30 h
13: 85 percent / Ag2O / dimethylformamide / 2 h / Ambient temperature
14: 90 percent / N-methylmorpholine N-oxide, OsO4 / CH2Cl2; tetrahydrofuran; H2O / 20 h / Ambient temperature
15: 88 percent / DBU / benzene / 1.5 h / Heating
16: 63 percent / acetonitrile / 0.08 h / 0 °C
17: 88 percent / N-methylmorpholine N-oxide, OsO4 / CH2Cl2; tetrahydrofuran; H2O / 12 h / Ambient temperature
18: 1.) Bu2SnO, 3-Angstroem molecular sieves, 2.) Bu4N(1+)I(1-) / 1.) toluene, 1 h, reflux, 2.) toluene, 80 deg C, 3.5 h
19: 95 percent / Ag2O / dimethylformamide / 16 h / Ambient temperature
20: 75 percent / DDQ / CH2Cl2; H2O / 3.5 h / Ambient temperature
21: 81 percent / Zn, aq. acetic acid / CH2Cl2 / 48 h / Heating
22: 1.) NaH / 1.) THF, 0 deg C, 5 min, 2.) THF, 0 deg C to room temp., 2 h
23: 56 percent / 1.2 h / 100 - 105 °C / 0.05 - 0.1 Torr
24: 75 percent / N-methylmorpholine N-oxide, OsO4 / tetrahydrofuran; H2O / 45 h / Ambient temperature
With
1H-imidazole; dmap; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; 3 A molecular sieve; tetrabutyl ammonium fluoride; iodine; sec.-butyllithium; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; acetic acid; methanesulfonyl chloride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; bis(tri-n-butyltin)oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(II) oxide; silver(l) oxide; zinc;
amberlyst-15;
In
tetrahydrofuran; diethyl ether; dichloromethane; chloroform; cyclohexane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1021/ja00195a039