Multi-step reaction with 13 steps
1: 91 percent / KI / acetone; H2O / 24 h / Heating
2: 56 percent / toluene / 8 h / 180 °C
3: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, RT, 30 min
4: polyphosphoric acid / benzene / 6 h / Heating
5: 24.3 g / pyridinium hydrochloride / 2 h / 170 °C
6: NaH / dimethylformamide / 5 h / 24 °C
7: H2 / PtO2 / ethyl acetate / 1.5 h / 1034.3 Torr
8: dioxane / 3 h / Heating
9: 92 percent / N-bromosuccinimide, H2SO4 / tetrahydrofuran / 5 h / -61 °C
10: 96 percent / NaH / toluene; dimethylformamide / 3 h / Ambient temperature
11: n-Bu3SnH, AIBN / benzene / 0.58 h / Heating
12: 1.) monoisopinocampheylborane, 2.) 2N aq. NaOH, 30percent aq. H2O2 / 1.) THF, RT, 2 h, 2.) THF, a) RT, 1 h, b) 50 deg C, 20 min
13: 100 percent / Ph3P, CCl4 / CH2Cl2 / Ambient temperature
With
tetrachloromethane; sodium hydroxide; N-Bromosuccinimide; PPA; dimethylsulfide; 2,2'-azobis(isobutyronitrile); sulfuric acid; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; pyridine hydrochloride; sodium hydride; ozone; triphenylphosphine; potassium iodide; (-)-Monoisopinocampheylborane;
platinum(IV) oxide;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1021/jm00028a005