Multi-step reaction with 15 steps
1: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h
2: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h
3: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C
4: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr
6: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C
7: 76 percent / PS-30 catalyst / various solvent(s) / 48 h
8: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h
9: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature
10: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h
11: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C
12: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C
13: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C
14: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C
15: pyridine / 2 h / 20 - 25 °C
With
palladium diacetate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; chloro-trimethyl-silane; 4-acetoxy-2,2,6,6-tetramethylpiperidine-1-oxyl; trimethylamine-N-oxide; PS-30 catalyst; parathion; potassium tert-butylate; tetrabutyl-ammonium chloride; hydrogen; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; sodium iodide; potassium bromide;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; trifluoroacetic acid; tert-butyl alcohol;
DOI:10.1021/jo970173f