1: With diisobutylaluminium hydride in tetrahydrofuran; toluene T=-78°C; 3.5 h; 2: With hydrogenchloride in tetrahydrofuran T=-78 - 20°C;

1: 3-bromo-furan With n-butyllithium in diethyl ether; hexane T=-78°C; 0.25 h; 2: γ-bicyclohomofarnesal in diethyl ether; hexane T=-78°C; 2 h;

1: With pyridine; thionyl chloride in dichloromethane T=-78°C; 0.75 h; 2: With lithium aluminium tetrahydride in tetrahydrofuran 0.5 h; Further stages.;

1.1: n-BuLi / tetrahydrofuran / 0.08 h / -78 °C 1.2: 85 percent / tetrahydrofuran / 0.33 h / -78 - -40 °C 2.1: pyridine; thionyl chloride / CH2Cl2 / 0.75 h / -78 °C 2.2: LiAlH4 / tetrahydrofuran / 0.5 h View Scheme

1.1: 91 percent / aq. HCl / tetrahydrofuran / 0.5 h / 20 °C 2.1: DIBAL-H / tetrahydrofuran; toluene / 3.5 h / -78 °C 2.2: 84 percent / aq. HCl / tetrahydrofuran / -78 - 20 °C View Scheme

1.1: n-BuLi / diethyl ether; hexane / 0.83 h / -78 - -23 °C 1.2: ClTi(OiPr)3 / diethyl ether; hexane / 0.25 h / -78 - -20 °C 1.3: 72 percent / diethyl ether; hexane / 4 h / -110 - -78 °C 2.1: 91 percent / aq. HCl / tetrahydrofuran / 0.5 h / 20 °C 3.1: DIBAL-H / tetrahydrofuran; toluene / 3.5 h / -78 °C 3.2: 84 percent / aq. HCl / tetrahydrofuran / -78 - 20 °C View Scheme

1.1: 88 percent / pyridine; thionyl chloride / CH2Cl2 / 0.5 h / -78 °C 2.1: 91 percent / DIBAL / diethyl ether; tetrahydrofuran / 2 h / -78 - -20 °C 3.1: n-BuLi / diethyl ether; hexane / 0.83 h / -78 - -23 °C 3.2: ClTi(OiPr)3 / diethyl ether; hexane / 0.25 h / -78 - -20 °C 3.3: 72 percent / diethyl ether; hexane / 4 h / -110 - -78 °C 4.1: 91 percent / aq. HCl / tetrahydrofuran / 0.5 h / 20 °C 5.1: DIBAL-H / tetrahydrofuran; toluene / 3.5 h / -78 °C 5.2: 84 percent / aq. HCl / tetrahydrofuran / -78 - 20 °C View Scheme

1.1: 91 percent / DIBAL / diethyl ether; tetrahydrofuran / 2 h / -78 - -20 °C 2.1: n-BuLi / diethyl ether; hexane / 0.83 h / -78 - -23 °C 2.2: ClTi(OiPr)3 / diethyl ether; hexane / 0.25 h / -78 - -20 °C 2.3: 72 percent / diethyl ether; hexane / 4 h / -110 - -78 °C 3.1: 91 percent / aq. HCl / tetrahydrofuran / 0.5 h / 20 °C 4.1: DIBAL-H / tetrahydrofuran; toluene / 3.5 h / -78 °C 4.2: 84 percent / aq. HCl / tetrahydrofuran / -78 - 20 °C View Scheme

lithium aluminium tetrahydride