Multi-step reaction with 12 steps
1: 97 percent / NaAl(CH3OCH2CH2O)2H2 (Red-Al)
2: 64 percent / t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Ambient temperature
3: 77 percent / Me2AlNH2 / xylene / 100 °C
4: 97 percent / DMSO, (COCl)2, Et3N / CH2Cl2
5: 1.) LDA / 1.) THF, -100 deg C, 2.) -95 deg C, 30 min
6: pyridine, DMAP
7: DBU / Ambient temperature
8: 34 percent / acetone / 0 °C / Irradiation
9: (i-Bu)2AlH (DIBALH) / toluene
10: imidazole
11: 80 percent / ZrCl4 / CH2Cl2 / 0.25 h / 0 °C
12: 1.) n-Bu4NF (TBAF), 2.) HF / 1.) THF, 2.) CH3CN
With
pyridine; 1H-imidazole; dmap; oxalyl dichloride; dimethylaluminium amide; hydrogen fluoride; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide;
zirconium(IV) chloride;
In
tetrahydrofuran; dichloromethane; acetone; toluene; xylene; tert-butyl alcohol;
DOI:10.1016/S0040-4039(00)60377-5