Multi-step reaction with 28 steps
1: 84 percent / I2, PPh3, imidazole / acetonitrile / 0.5 h / 25 °C
2: 90 percent / acetonitrile / 48 h / 80 °C
3: 1) n-BuLi / 1) THF, -78 deg C, 1 h, 2) HMPA, -78 deg C - 25 deg C, 18 h
4: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 25 °C
5: 74 percent / AgCO4, NaHCO3, 4 Angstroem molecular sieve, silicagel / nitromethane / 4 h / 25 °C
6: 95 percent / Ph3SnH, AIBN / toluene / 2 h / 110 °C
7: 85 percent / DIBAH / CH2Cl2 / 1 h / -78 °C
8: NEt3 / CH2Cl2 / 1 h / 0 °C
9: DBU / dimethylformamide / 2 h / 145 °C
10: m-chloroperbenzoic acid / tetrahydrofuran; H2O / 1 h / 0 - 25 °C
11: NaBH4 / methanol / 1 h / 0 °C
12: 1) NaIO4, 2) NaBH4 / 1) EtOH, H2O, 25 deg C, 1 h, 2) MeOH, 0 deg C, 1 h
13: 82 percent / pyridine / 4 h / -20 - 0 °C
14: 97 percent / imidazole / dimethylformamide / 12 h / 25 °C
15: 98 percent / DIBAH / CH2Cl2 / 1 h / -78 °C
16: NEt3 / CH2Cl2 / 1 h / 0 °C
17: NaI / acetone / 2 h / 56 °C
18: 92 percent / iodine / acetonitrile / 48 h / 60 °C
19: 1) n-BuLi, 2) HMPA / 1) THF, -78 - 0 deg C, 20 min, 2) -78 - 25 deg C, 3 h
20: tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 25 °C
21: imidazole / dimethylformamide / 3 h / 0 °C
22: 87 percent / AgClO4, NaHCO3, silicagel, 3 Angstroem molecular sieve / nitromethane / 3 h / 25 °C
23: m-chloroperbenzoic acid, NaHCO3 / CH2Cl2 / 0 °C
24: CH2Cl2 / 0.5 h / -78 °C
25: 90 percent / EtSH, Zn(OTf)2, NaHCO3 / CH2Cl2 / 5 h / 25 °C
26: 86 percent / pyridine / 12 h / 0 °C
27: 75 percent / m-chloroperbenzoic acid / CH2Cl2 / 3 h / 0 °C
28: 82 percent / 2,6-lutidine / CH2Cl2 / 0.33 h / 0 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; 4 A molecular sieve; triphenylstannane; tetrabutyl ammonium fluoride; iodine; silver perchlorate; silica gel; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; ethanethiol; sodium iodide;
In
tetrahydrofuran; methanol; nitromethane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;