Multi-step reaction with 15 steps
1: 22.9 percent / TsOH / toluene; dimethylformamide / 2 h / 143 °C
2: 64.5 percent / KOH / 3.5 h / 100 - 125 °C
3: 80.4 percent / 1,2-dihydroxyethane, TsOH / CH2Cl2 / 0.78 h / 24 °C
4: NaH / dimethylformamide / 1 h / 25 - 60 °C
5: 1M aq. HCl / ethanol; toluene / 2.5 h / 60 °C
6: 1.) Bu2SnO / 1.) toluene, 100 deg C, 45 min; 2.) DMF, 95 deg C, 1.5 h
7: 61.6 percent / NaH / dimethylformamide / 2 h / 25 - 40 °C
8: 82 percent / t-BuOK / dimethylsulfoxide / 19 h / 50 °C
9: 83 percent / 1M aq. HCl / ethanol; toluene / 8.5 h / 23 °C
10: 59 percent / pyridinium chlorochromate / CH2Cl2 / 19 h / 25 °C
11: 95 percent / BuLi / tetrahydrofuran / 0.37 h / 0 - 22 °C
12: 1.) BH3*Me2S; 2.) 5M NaOH, 30percent H2O2 / 1.) toluene, 25 - 68 deg C, 1.5 h; 2.) EtOH, 75 deg C, 5 min
13: 99 percent / pyridine / DMAP / CH2Cl2 / 1 h / 25 °C
14: 45 percent / DDQ, H2O / CH2Cl2 / 1.5 h / 25 °C
15: 1.) 1H-tetrazole; 2.) m-chloroperbenzoic acid / 1.) CH2Cl2, 25 deg C, 2.5 h; 2.) -40 deg C to RT, 1.5 h
With
pyridine; 1H-tetrazole; hydrogenchloride; potassium hydroxide; sodium hydroxide; n-butyllithium; dimethylsulfide borane complex; potassium tert-butylate; water; dihydrogen peroxide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; ethylene glycol; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
dmap;
In
tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.19900730428