Multi-step reaction with 8 steps
1.1: 91 percent / NaH
2.1: TMEDA; n-BuLi / tetrahydrofuran / 4 h / 20 °C
2.2: 77 percent / tetrahydrofuran / 2 h
3.1: NaH / toluene / 0.25 h / 20 °C
3.2: 86 percent / toluene / 12 h / 20 °C
4.1: H2 / Pd/C / ethyl acetate / 12 h
4.2: 3.69 g / DIBAL-H / CH2Cl2 / 1 h / 0 °C
5.1: NH4NO3; (CF3CO)2O / acetonitrile / 0.25 h / 20 °C
5.2: 67 percent / LiOH / tetrahydrofuran; methanol; H2O / 0.08 h
6.1: 82 percent / PPh3; diisopropyl azodicarboxylate / tetrahydrofuran / 10 h / 0 - 20 °C
7.1: OsO4; NaIO4; 2,6-lutidine / dioxane; H2O / 2 h / 20 °C
8.1: 313 mg / 2-methyl-2-butene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
With
ammonium nitrate; 2,6-dimethylpyridine; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; 2-methyl-but-2-ene; N,N,N,N,-tetramethylethylenediamine; di-isopropyl azodicarboxylate; hydrogen; sodium hydride; triphenylphosphine; trifluoroacetic anhydride;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; water; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol;
6.1: Mitsunobu esterification;
DOI:10.1021/jo061054f