Multi-step reaction with 10 steps
1: 83 percent / LiAlH4 / tetrahydrofuran / 22 h / Heating
2: 80 percent / CrO3, pyridine / CH2Cl2 / 0.33 h
3: 92 percent / toluensulphonic acid / benzene / 4 h / Heating
4: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) -78 deg C -> -22 deg C, 2 h
5: 99 percent / pyridine / 40 h / 6 °C
6: chloramine-T / tetrahydrofuran / 1 h
7: 2,6-di-tert-butylpyridine, NaI / acetone / 17.5 h / 54 °C
8: 1.) LDA / 1.) DME, -78 deg C, 12 min, 2.) -78 deg C, 2 h
9: 1.) LDA / 1.) DME, -78 deg C, 10 min, 2.) -78 deg C -> 0 deg C, 25 min
10: 1.) m-CPBA, 2.) pyridine, 3.) Me2S, 4.) PhSH, NEt3
With
pyridine; chromium(VI) oxide; lithium aluminium tetrahydride; 2,6-di-tert-butyl-pyridine; dimethylsulfide; chloroamine-T; toluene-4-sulfonic acid; thiophenol; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; lithium diisopropyl amide;
In
tetrahydrofuran; dichloromethane; acetone; benzene;
DOI:10.1021/ja00401a032