1: 94 percent / Br2 / 40 °C 2: 84 percent / NaOMe / methanol / Heating View Scheme

sodium methylate in methanol Heating;

potassium hydroxide; ammonium chloride; diethylene glycol T=200°C;

sulfuric acid in tetrahydrofuran T=25°C; 0.333333 h;

1.1: 9-BBN / tetrahydrofuran / 48 h / 20 °C 1.2: 82 percent / NaOH; aq. H2O2 / tetrahydrofuran; ethanol / 1 h / Heating 2.1: 85 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 - -10 °C 3.1: H2SO4 / diethyl ether; CHCl3 View Scheme

1: m-chloroperbenzoic acid 2: 93 percent / Zn, chlorotrimethylsilane / CH2Cl2 / 0.5 h / 0 °C 3: 77 percent / pyridine, Cr2O3, kieselguhr / CH2Cl2 / 0.33 h / Ambient temperature 4: 79 percent / silica gel, 15percent H2SO4 / CH2Cl2 / 24 h / Ambient temperature View Scheme

1.1: 9-BBN / tetrahydrofuran / 48 h / 20 °C 1.2: 82 percent / NaOH; aq. H2O2 / tetrahydrofuran; ethanol / 1 h / Heating 2.1: 85 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 - -10 °C 3.1: H2SO4 / diethyl ether; CHCl3 4.1: 9.56 g / p-TsOH / CHCl3 / 36 h / Heating 5.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 5.2: 51 percent / tetrahydrofuran; hexane / 13.5 h / -78 - 20 °C 6.1: 34 percent / LiAlH4 / diethyl ether / 3 h / Heating View Scheme

1.1: 9-BBN / tetrahydrofuran / 48 h / 20 °C 1.2: 82 percent / NaOH; aq. H2O2 / tetrahydrofuran; ethanol / 1 h / Heating 2.1: 85 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 - -10 °C 3.1: H2SO4 / diethyl ether; CHCl3 4.1: 9.56 g / p-TsOH / CHCl3 / 36 h / Heating 5.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 5.2: 51 percent / tetrahydrofuran; hexane / 13.5 h / -78 - 20 °C View Scheme

1: m-chloroperbenzoic acid 2: 93 percent / Zn, chlorotrimethylsilane / CH2Cl2 / 0.5 h / 0 °C 3: 77 percent / pyridine, Cr2O3, kieselguhr / CH2Cl2 / 0.33 h / Ambient temperature View Scheme

1: With 9-borabicyclo[3.3.1]nonane dimer in tetrahydrofuran T=20°C; 48 h; 2: With sodium hydroxide; dihydrogen peroxide in tetrahydrofuran; ethanol 1 h; Heating; Further stages.;