potassium tert-butylate in tetrahydrofuran T=20°C; 24 h;

sulfuric acid; sodium methylate in anhydrous xylene; water

1.1: 87 percent / hydroxylamine hydrochloride; NaOH / ethanol; H2O / 3 h / Heating 2.1: 88 percent / LiAlH4; diisopropylamine / tetrahydrofuran / 4 h / Heating 3.1: 85 percent / triethylamine / tetrahydrofuran / 3 h / 25 °C 4.1: 76 percent / Cs2CO3 / dioxane / 18 h / Heating 5.1: 75 percent / Cs2CO3 / acetonitrile / 20 h / 25 °C 6.1: AgOTf / CH2Cl2 / 1 h / 25 °C 6.2: 77 percent / TBAT / CH2Cl2 / 20 h / -45 - 25 °C 7.1: 74 percent / samarium diiodide; HMPA / 2-methyl-propan-2-ol / 3 h / -78 - -45 °C 8.1: 99 percent / Schwartz's reagent / tetrahydrofuran / 16 h / Heating 9.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C 10.1: 99 percent / HCl; methanol / 16 h / 25 °C 11.1: Yb(OTf)3*xH2O / CH2Cl2 / 48 h / 0 °C 11.2: 50 percent / ortho-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 25 °C 12.1: 42 percent / chromium(II) chloride / acetone; H2O / 1 h / 25 °C 13.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 25 °C 14.1: 55 percent / pTsOH*H2O / CH2Cl2 / 7 h / 0 - 25 °C 15.1: 95 percent / NaBH4; MeOH / 1.17 h / -78 - 25 °C View Scheme

(NH4)2S2O8; [{(η5-C5Me5)RhCl}2(μ-Cl)2] in water T=110°C; 3 h; Inert atmosphereSealed tube;

in methanol; dimethyl sulfoxide; N,N-dimethyl-formamide T=150°C; 6 h;

sodium hydroxide in methanol 10 h; Ambient temperature;

1: With N-ethyl-N,N-diisopropylamine in dichloromethane T=20°C; Aldol reaction; 0.0833333 h; Inert atmosphere; 2: With titanium tetrachloride in dichloromethane T=-25 - -10°C; Aldol reaction; Inert atmosphere;

nitric acid in nitromethane T=20°C; 2.5 h;

nitric acid in water; acetic acid T=3 - 20°C; Nitration; deacetylation; 3.75 h; Title compound not separated from byproducts;

1: 84 percent / p-TsOH*H2O; NBS / acetonitrile / Heating 2: 73 percent / sodium azide / dimethylsulfoxide / 25 °C View Scheme