1.1: pyridine / 12 h / 0 - 20 °C / |Inert atmosphere 2.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C 3.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / |Inert atmosphere 5.1: N,N-dimethyl-formamide / 18 h / 20 °C / |Darkness 6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 6.2: -78 - 20 °C 7.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 8.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere; |Cooling with acetone-dry ice 9.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / |Inert atmosphere; |Cooling with acetone-dry ice 10.1: Pd(1,2-bis(diphenylphosphino)ethane)Cl2 / tetrahydrofuran / 0.08 h / 0 °C / |Cooling with acetone-dry ice; |Inert atmosphere 10.2: 4.5 h / 0 °C / |Inert atmosphere 11.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme

sodium carbonate; magnesium chloride in terpene synthase buffer T=25°C; pH=10; 18 h; Enzymatic reaction;

sodium acetate; magnesium chloride in terpene synthase buffer T=25°C; pH=5; 18 h; Enzymatic reaction;

potassium chloride in terpene synthase buffer T=25°C; pH=8; 18 h; Enzymatic reaction;

potassium chloride in terpene synthase buffer T=37°C; pH=8; 18 h; Enzymatic reaction;

pyridinium chlorochromate in dichloromethane T=20°C; 24 h;

di-isopropyl azodicarboxylate; triphenylphosphine in tetrahydrofuran T=10 - 20°C; Mitsunobu reaction; sonication;

1: various solvent(s) 2: H2 / PtO2 3: OH(1-) / Heating 5: 400 °C View Scheme

1: tBuOOH, VO(acac)2 / benzene / under standard Sharpless conditions 2: lithium diethylamide / benzene / Heating 3: pyridine / 1.5 h / Ambient temperature 4: sodium bicarbonate / methanol 5: DIBAL / tetrahydrofuran / 2 h / ice bath 6: 73 percent / tBuOOH, VO(acac)2 / benzene / under standard Sharpless conditions 7: CrO3-pyridine / CH2Cl2 / Ambient temperature 8: silica gel / eluted the column with hexane-ether View Scheme

di-isopropyl azodicarboxylate; triphenylphosphine in tetrahydrofuran T=10 - 20°C; Mitsunobu reaction; sonication;