1: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C 2: p-toluenesulfonic acid / methanol / 1 h / 0 °C 3: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h View Scheme

1: p-toluenesulfonic acid / methanol / 1 h / 0 °C 2: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h View Scheme

1: 70 percent / diethyl ether / -10 °C 2: 90 percent / triphenylphosphine, carbon tetrachloride / 12 h / Heating 3: diisobutylaluminium hydride / tetrahydrofuran / -40 °C 4: manganese dioxide / hexane / Ambient temperature 5: KCN, 18-crown-6 / 1 h / 0 °C 6: trimethylbenzylammonium fluoride / tetrahydrofuran; H2O / 0 °C 8: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C 9: p-toluenesulfonic acid / methanol / 1 h / 0 °C 10: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h View Scheme

biotransformation by suspension cultured cells of Solidago altissima; Further byproducts given;

biotransformation by suspension cultured cells of Polygonum tinctorium; further cultured cells: Solidago altissima; Further byproducts given;

Mucor alternata in water 84 h; Further byproducts.;

1.1: bis(benzonitrile)palladium(II) dichloride / toluene / 1 h / Reflux; Inert atmosphere 2.1: pyridine; potassium tert-butylate / 0.08 h / Inert atmosphere; Reflux 2.2: 0 - 20 °C / Inert atmosphere 3.1: carbon disulfide; sodium hydride; methyl iodide / tetrahydrofuran; mineral oil / 0 - 20 °C 3.2: 0.25 h / Inert atmosphere; Reflux View Scheme

1.1: (S)-Corey-Bakshi-Shibata reagent; borane-THF / tetrahydrofuran; toluene / Cooling with ice; Inert atmosphere 2.1: bis(benzonitrile)palladium(II) dichloride / toluene / 1.75 h / Inert atmosphere; Reflux 3.1: ammonia; sodium / tetrahydrofuran / 0.42 h / -78 °C 3.2: 0.08 h View Scheme

1.1: (S)-Corey-Bakshi-Shibata reagent; borane-THF / tetrahydrofuran; toluene / Cooling with ice; Inert atmosphere 2.1: bis(benzonitrile)palladium(II) dichloride / toluene / 1.75 h / Inert atmosphere; Reflux 3.1: ammonia; sodium / tetrahydrofuran / 0.42 h / -78 °C 3.2: 0.08 h View Scheme

acetophenone in diethyl ether Irradiation;