Multi-step reaction with 14 steps
1: triethylamine / H2O; dioxane / 3 h / Ambient temperature
2: 100 percent / diethyl ether; methanol
3: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
4: 70 percent / imidazole / dimethylformamide / 1.) 0 deg C, 30 min; 2.) r.t., 30 min
5: 97 percent / mCPBA / CH2Cl2 / Ambient temperature
6: lithium tetramethylpiperidine / diethyl ether / 1.) 0 deg C, 1 h; 2.) r.t., 1 h
7: 86 percent / MnO2 / hexane / 1 h / Ambient temperature
8: 93 percent / triethylamine / tetrahydrofuran / 1 h / 0 °C
9: 98 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C
10: 99 percent / DIBAH / hexane; toluene / 0.33 h / 0 °C
11: 98 percent / Na2HPO4, NaIO4 / H2O; methanol / 1 h / 40 °C
13: 87 percent / tetrahydrofuran; diethyl ether / 0.5 h / -15 °C
14: 83 percent / PDC / dimethylformamide / Ambient temperature
With
1H-imidazole; manganese(IV) oxide; sodium periodate; disodium hydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; 2,2,6,6-tetramethylpiperidinyl-lithium; sodium hydride; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00222a044