Multi-step reaction with 18 steps
1: p-TsOH*H2O / diethyl ether
2: LiAlH4 / diethyl ether
3: p-TsOH*H2O / methanol
4: 98.3 g / p-TsOH*H2O / acetone
5: 97 percent / pyridinium chlorochromate, MS (3 Angstroem) / CH2Cl2
6: 64 percent / p-TsOH*H2O / CH2Cl2 / Heating
7: 72 percent / pyridinium dichromate, MS (3 Angstroem) / CH2Cl2
8: 1.) LDA, HMPA, 2.) HMPA / 1.) hexane/THF, -76 -72 deg C, 13 min, then -35 deg C, 2.) -78 deg C, 15 min
9: 11 percent / sucrose, phosphate buffer, baker's yeast, 0.2 percent Triton -100 aq. / 1 h / 30 °C
10: p-TsOH*H2O / ethanol; H2O / 168 h / Ambient temperature
11: 4-(N,N-dimethylamino)pyridine / pyridine
12: 97 percent / LAH / diethyl ether
13: 80 percent / NaH (60 percent), n-Bu4N(1+)*I(1-) / paraffin; tetrahydrofuran / 1 h / Heating
14: acetonitrile / 1 h / Heating
15: 1.) HMPA, n-BuLi / 1.) THF/n-hexane, -67 deg C, 30 min, 2.) THF, -67 -63 deg C, then room temperature, 3 h 50 min and 6 h 15 min
16: HCl, H2O / tetrahydrofuran / 15 h / Ambient temperature
17: 75 percent / Na, liq. NH3 / tetrahydrofuran
18: 18 percent / DMAP / pyridine / 72 h / Ambient temperature
With
hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; baker's yeast; phosphate buffer; MS (3 Angstroem); Triton -100; ammonia; water; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; Sucrose;
toluene-4-sulfonic acid;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; acetonitrile; paraffin;
DOI:10.1016/S0040-4020(01)89929-4