2,6-dimethylpyridine in dichloromethane T=0°C; 0.25 h;

1H-imidazole in dichloromethane T=20°C;

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.25 h / 20 °C / Inert atmosphere 1.2: 24 h / Inert atmosphere; Reflux 2.1: sec.-butyllithium / diethyl ether; hexane; cyclohexane / 1 h / -78 °C / Inert atmosphere 2.2: 2 h / -78 °C / Inert atmosphere 3.1: cesium fluoride / dichloromethane; water / 16 h / 20 °C 4.1: tetrahydrofuran / 2 h / 20 °C 5.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 20 °C 6.1: Jone's reagent / acetone / 0 - 20 °C 7.1: chlorosulfonic acid / dichloromethane / 0.75 h / 20 °C 8.1: sodium acetate / ethanol / 15 h / Reflux 8.2: 20 h / 20 °C / 760.05 Torr View Scheme

1: sodium hydride / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 16 h / 0 - 20 °C / |Inert atmosphere 2: sodium carbonate / n-heptane / 16 h / 0 °C / |Inert atmosphere 3: sodium periodate; osmium(VIII) oxide / diethyl ether; water-d2 / 16 h 4: sodium tetrahydroborate / methanol; diethyl ether / 0 °C / |Inert atmosphere View Scheme

Multistep reaction;

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.25 h / 20 °C / Inert atmosphere 1.2: 24 h / Inert atmosphere; Reflux 2.1: sec.-butyllithium / diethyl ether; hexane; cyclohexane / 1 h / -78 °C / Inert atmosphere 2.2: 2 h / -78 °C / Inert atmosphere 3.1: cesium fluoride / dichloromethane; water / 16 h / 20 °C 4.1: tetrahydrofuran / 2 h / 20 °C 5.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 20 °C 6.1: Jone's reagent / acetone / 0 - 20 °C 7.1: chlorosulfonic acid / dichloromethane / 0.75 h / 20 °C View Scheme

hydrogen; platinum on activated charcoal in methanol Ambient temperature;

1: allyl bromide With pyridine; indium; (1S,2R)-(+)-erythro-2-amino-1,2-diphenylethanol in tetrahydrofuran T=25°C; Barbier type asymmetric allylation; 0.5 h; Inert atmosphere; 2: benzaldehyde in tetrahydrofuran; hexane T=-78°C; Barbier type asymmetric allylation; 2 h; Inert atmosphere; 3: With water; ammonium chloride in tetrahydrofuran; hexane T=-78 - 25°C; Inert atmosphere; optical yield given as percent eeenantioselective reaction;

C48H53O4P in toluene T=-30°C; Inert atmosphere; enantioselective reaction;

terpene-derived pyridine N-oxide; N-ethyl-N,N-diisopropylamine in acetonitrile T=-40°C; 18 h;