Multi-step reaction with 15 steps
1: 1.) sodium hydride / 1.) DME, RT, 10 min; 2.) DME, RT, overnight
2: 1.) TMEDA, n-BuLi 2.) ClTi(O-iPr)3 / 1.) ether, hexane, -78 deg C, 1 h 2.) ether, hexane, -78 deg C, 2 h then -10 deg C, 1.5 h
3: LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C / Heating
4: PPTS / CH2Cl2 / 0.08 h / Ambient temperature
5: 1.) B2H6, 2-methyl-2-butene 3.) 3M NaOH, 30percent aq. H2O2 / 1.) THF, -10 deg C, 2 h 2.) THF, 0 deg C, 30 min; 3.) THF, RT, 30 min.
6: 90 percent / triphenylphosphine, imidazole, I2 / tetrahydrofuran; acetonitrile / 0.5 h / -10 °C
7: 1.) NaH / 1.) DMSO, RT, 30 min; 2.) DMSO, overnight
8: MeOH / PPTS / 0.08 h / Heating
9: 1.) DMSO, (COCl)2 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min; 2.) CH2Cl2, -78 to 0 deg C
10: 35 percent / K2CO3, 18-crown-6 / toluene / 80 °C
11: H2O / PPTS / tetrahydrofuran / 1.5 h / Heating
12: PCC, sodium acetate / CH2Cl2 / 2.5 h
13: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min.
14: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C
15: 90 percent / KOH / aq. ethanol / 3 h / Heating
With
1H-imidazole; triisopropoxytitanium(IV) chloride; methanol; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; 1,10-Phenanthroline; 2-methyl-but-2-ene; oxalyl dichloride; 18-crown-6 ether; N,N,N,N,-tetramethylethylenediamine; water; dihydrogen peroxide; iodine; sodium acetate; N-cyclohexyl-N'-β-(4-methylmorpholinium)ethylcarbodiimide p-toluenesulfonate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; pyridinium chlorochromate; diborane; lithium diisopropyl amide;
pyridinium p-toluenesulfonate; copper(II) iodide;
In
tetrahydrofuran; ethanol; dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0040-4020(01)87668-7