methanol; Na-SG in tetrahydrofuran T=0 - 25°C; Bouveault-Blanc reduction; Inert atmosphere;

tert.-butylhydroperoxide; potassium tert-butylate; tetrabutyl ammonium fluoride in tetrahydrofuran; decane T=70°C; Inert atmosphereMolecular sieve;

hydrogen; platinum(IV) oxide in ethanol

lithium aluminium tetrahydride in tetrahydrofuran; monofluoro-trichloromethane T=0°C; Yield given;

(i) ClCO2Et, Et3N, THF, (ii) aq. NaBH4; Multistep reaction;

1: [1,3-bis(diphenylphosphino) propane] dichloronickel(II) / tetrahydrofuran / 6 h / 80 °C / Inert atmosphere 2: bis(η4-1,5-cyclooctadiene)-di-μ-methoxy-diiridium(I); bicyclo-[2.2.1]hept-2-ene; 4,4'-di-tert-butyl-2,2'-dipyridyl / tetrahydrofuran / 12 h / 80 °C / Inert atmosphere 3: tert.-butylhydroperoxide; potassium tert-butylate; tetrabutyl ammonium fluoride / tetrahydrofuran; decane / 70 °C / Inert atmosphere; Molecular sieve View Scheme

oxygen in ethanol T=30°C; Sealed vialEnzymatic reaction; regioselective reaction;

1: bis(η4-1,5-cyclooctadiene)-di-μ-methoxy-diiridium(I); bicyclo-[2.2.1]hept-2-ene; 4,4'-di-tert-butyl-2,2'-dipyridyl / tetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: tert.-butylhydroperoxide; potassium tert-butylate; tetrabutyl ammonium fluoride / tetrahydrofuran; decane / 70 °C / Inert atmosphere; Molecular sieve View Scheme

n-butyllithium; diethyl ether anschliessendes Behandeln mit Aethylenoxid und Erwaermen des Reaktionsprodukts mit wss.-methanol. HCl;

1: aqueous hydrochloric acid 2: butyl lithium; diethyl ether / anschliessendes Behandeln mit Aethylenoxid und Erwaermen des Reaktionsprodukts mit wss.-methanol. HCl View Scheme