Multi-step reaction with 25 steps
2: Wittig methylenation
3: 72 percent / CHCl3 / 30 h / 23 °C
4: BF3*Et2O / -35 deg C, 1 h, 0 deg C, 15 min
5: DBN / 0.75 h / 23 °C
6: O2 / 0.1percent methylene blue / CHCl3 / 144 h / 0 °C / Irradiation
7: 97 percent / AlHg / tetrahydrofuran; H2O / 0.17 h / 23 °C
8: 85 percent / DMAP / 1,2-dichloro-ethane / 2 h / 50 °C
9: 1.) pyridinium chlorochromate, 2.) AlHg / 1.) 1,2-dichloroethane, 80 to 90 deg C, 5 h, 2.) THF - H2O, 20 deg C, 18 min
10: 99 percent / diethyl ether
11: diisobutylaluminumhydride / toluene / 1.25 h / -78 °C
12: tert-butyl hydroperoxide / Mo(CO)6 / benzene / 1 h / 68 °C
13: KOH / methanol / 0.17 h / 23 °C
14: 99 percent / tosic acid / acetone / 1.5 h / 23 °C
15: 80 percent / tetrahydrofuran / 0 °C
16: 60 percent / 2,6-lutidine, silver triflate / CH2Cl2 / 23 °C
17: 1.) K2CO3, 2.) oxalic acid / 1.) THF - ethylene glycol, 23 deg C, 2 h, 2.) water - aceton, 60 deg C, 7 h
18: imidazole / dimethylformamide / 0.5 h / 23 °C
19: 82 percent / 1.) thallous ethoxide / 1.) 23 deg C, 30 min, 2.) -78 to 45 deg C, 1 h
20: 63 percent / O2 / methylene blue / CHCl3 / 5 h / 10 °C / Irradiation
21: 80 percent / NaOCH3, Bu3P / ethanol / 2.5 h / 0 °C
22: acetic acid / 23 h / 100 - 105 °C / in sealed tube
23: 85 percent / BF3*Et2O / diethyl ether / -78deg C, 4 h, -50 deg C, 15 min
24: 2percent HF / acetonitrile; H2O / 0.25 h / 0 °C
25: n-Bu3P / tetrahydrofuran / 2 h / 0 °C
With
1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; potassium hydroxide; tributylphosphine; aluminium amalgam; 2,6-dichloro-benzonitrile; boron trifluoride diethyl etherate; hydrogen fluoride; oxygen; sodium methylate; silver trifluoromethanesulfonate; thallium (I) ethoxide; oxalic acid; diisobutylaluminium hydride; potassium carbonate; pyridinium chlorochromate;
hexacarbonyl molybdenum; methylene blue; toluene-4-sulfonic acid;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1021/ja00219a059