Multi-step reaction with 17 steps
1: 94 percent / imidazole / dimethylformamide / 36 h
2: 94 percent / H2 / Pd/C / acetic acid; ethanol / 24 h / 3102.9 Torr
3: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -50 deg C, 15 min, 2.) CH2Cl2, -50 deg C to r.t.
4: 89 percent / NaH / benzene / 1.) 1 h, 2.) 60 deg C, 3 h
5: 1.) n-BuLi, MgBr2*Et2O / 1.) hexane, benzene, THF, Et2O, - 78 deg C, 25 min; 2.) hexane, benzene, THF, Et2O, r.t., 1 h
6: 70 percent / lithium naphthalenide / tetrahydrofuran / -78 °C
7: 1.) n-BuLi / 1.) hexane, THF, 0 deg C, 20 min, 2.) THF, hexane, r.t., 3 h
8: 87 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
9: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -50 deg C, 15 min, 2.) CH2Cl2, -50 deg C to r.t.
10: 95 percent / CrCl2, NiBr2 / dimethylformamide / 48 h
11: 83 percent / Et3N / CH2Cl2 / 1 h
12: 96 percent / tricyclohexylphosphine, (CH3)3SiCl, DBU / toluene; acetonitrile / 16 h / 70 °C
13: 85 percent / diethyl ether / 0 °C
14: 90 percent / diisobutylaluminium hydride / hexane; tetrahydrofuran / 1 h / -78 °C
15: 81 percent / 4-methylmorpholine-N-oxide, 3 Angstroem molecular sieves, tetrapropylammonium perruthenate / CH2Cl2 / 2 h
16: 1.) LiHMDS / 1.) hexane, 0 deg C, 45 min, 2.) hexane, THF, -78 deg C, 1 h
17: 66 percent / diisopropylethylamine / CH2Cl2 / 1.6 h / Heating
With
1H-imidazole; chromium dichloride; n-butyllithium; chloro-trimethyl-silane; tetrapropylammonium perruthennate; oxalyl dichloride; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; naphthalen-1-yl-lithium; magnesium bromide; nickel dibromide; lithium hexamethyldisilazane; tricyclohexylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1039/a805856c
