1: piperidine 2: NaH 3: 45 percent / K2CO3 / acetone / Heating View Scheme

1: C9H10LiO(1-)*Li(1+) With zinc dibromide in tetrahydrofuran T=-78°C; 0.25 h; 2: cyclopent-2-enone in tetrahydrofuran T=-78°C; 3: With water in tetrahydrofuran

1: sodium carbonate / methanol / 24 h / 20 °C 2: sodium tetrahydroborate / tetrahydrofuran; methanol / 0 - 20 °C 3: hydrogenchloride / methanol / 2 h / |Reflux View Scheme

1.1: tert.-butyl lithium / diethyl ether / 2.25 h / -78 - 20 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: dipyridinium dichromate / dichloromethane / 24 h / 20 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere 4.1: MgBr2*Et2O; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere 4.2: 6 h / 20 °C / Inert atmosphere 5.1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C / Inert atmosphere 6.1: benzene / 24 h / Inert atmosphere; Reflux 7.1: (tricyclohexylphosphine)(1,5-cyclooctadiene)pyridineiridium(I) hexafluorophosphate; hydrogen / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere 8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere 9.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 10.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 10.2: 15.75 h / 0 - 20 °C / Inert atmosphere 11.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere View Scheme

1: (i) LDA, THF, (ii) /BRN= 1446054/ 2: aq. HCl View Scheme

sodium tetrahydroborate; azobisisobutyronitrile; tributyltin chloride; NAF 1) EtOH, r.t., 4 h, 2) H2O; Yield given. Multistep reaction;

1: (i) CuI, Et2O, (ii) /BRN= 1446054/, (iii) Cl2CHCO2H 2: KIO4, RuO4 / acetone 3: diethyl ether View Scheme

ferric nitrate

1: in diethyl ether T=0 - 20°C; 1 h; 2: With water; ammonium chloride in diethyl ether 3: With Celite; pyridinium chlorochromate in dichloromethane 3 h;

4-(N,N-dimethlyamino)pyridine; iodine; potassium carbonate in tetrahydrofuran 1 h;