Multi-step reaction with 13 steps
1: 1) LDA, HMPA / 1) THF, -78 deg C: 2) -20 deg C, 2 h
2: hexane / 504 h / Irradiation
3: NaBH4 / methanol / 1 h / -20 °C
4: 1) HCl, 2) NaIO4 aq / 1) MeOH, 1 h, RT; 2) H2O-MeOH, 30 min, 25 deg C
5: 98 percent / triethylamine / dimethylformamide / 2 h / Ambient temperature
6: 80 percent / LiEt3BH / tetrahydrofuran / 0.25 h / Ambient temperature
7: 96 percent / TsOH / 24 h / Ambient temperature
8: 93 percent / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C
9: 97 percent / Amberlite IR 120 / methanol / 24 h / Ambient temperature
10: O2 / Pt / H2O / 24 h / 50 °C
11: PCC / CH2Cl2 / 2 h / Ambient temperature
12: 80 percent / pyridine, SOCl2 / tetrahydrofuran / 0.5 h / 0 °C
13: 91 percent / NaBH4 / methanol / 0.5 h / 0 °C
With
pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; thionyl chloride; Amberlite IR 120; oxygen; lithium triethylborohydride; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide;
platinum;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)98812-X