1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tetrahydrofuran / 0.5 h / 50 °C / Inert atmosphere 2: sodium periodate / tetrahydrofuran; water / 0.17 h / 50 °C / Inert atmosphere 3: ammonium acetate; sodium acetate / tetrahydrofuran; water / 0.33 h / 50 °C / Inert atmosphere View Scheme

1: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C 2: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C 3: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C 4: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 15 h / 20 °C 5: CH2Cl2 / 2 h / 20 °C 6: H2; K2CO3 / Pd/C / ethanol / 20 °C / 4654.33 Torr 7: NaBH4; aq. NaOH / ethanol / 6 h / -10 °C 8: 2162 g / TsOH / methanol / 15 h / 0 - 20 °C 9: 80 percent / Ph2PH; n-BuLi / tetrahydrofuran; hexane / 20 h / Heating 10: 100 percent / K2CO3; tetrabutylammonium bromide / acetone / 8 h / Heating 11: 83 percent / aq. KOH / methanol / 3 h / Heating View Scheme

oxalyl dichloride; dimethyl sulfoxide; triethylamine in dichloromethane T=-78 - 20°C; Swern oxidation;

sodium hydride

1: 94 percent / imidazole / CH2Cl2 2: n-BuLi / hexane / 24 h / 0 - 20 °C 3: 4695 g / TBAF / tetrahydrofuran / 20 °C 4: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C View Scheme

1: n-BuLi / hexane / 24 h / 0 - 20 °C 2: 4695 g / TBAF / tetrahydrofuran / 20 °C 3: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C View Scheme

1: N,N-dimethylaniline / 230 °C 2: 84 percent / sodium hydride View Scheme

1: 93 percent / sodium hydride 2: N,N-dimethylaniline / 230 °C 3: 84 percent / sodium hydride View Scheme

1: 4695 g / TBAF / tetrahydrofuran / 20 °C 2: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C View Scheme

1: meta-hydroxybenzaldehyde; allyl bromide With dichloro-(phenyl)borane; lithium diisopropyl amide 2: methyl iodide