1: 95 percent / diisobutylaluminum hydride / toluene; hexane / 2.5 h / -25 - -20 °C 2: 91 percent / H2 / Pd/C / methanol / 12 h / 2585.74 Torr / Heating View Scheme

1: (R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one With sodium hydroxide in methanol; water T=70 - 80°C; 1 h; 2: dimethyl sulfate With tetrabutylammomium bromide in methanol; water T=40°C; 10 h; Title compound not separated from byproducts;

tetrakis-(ethylene)-μ,μ'-dichlorodirhodium(I); (R,R)-1,4-dimethyl-2,5-di(4'-methoxylphenyl)bicyclo[2.2.2]octane-2,5-diene; potassium hydroxide in 1,4-dioxane; water T=30°C; 3 h; Inert atmosphere; optical yield given as percent eeenantioselective reaction;

1: With sodium hydroxide; hydrogen; [RhCl(η2:η2-cycloocta-1,5-diene)]2 in methanol T=50°C; P=9000.9 Torr; 24 h; 2: With toluene-4-sulfonic acid in toluene 4 h; Heating; Further stages.;

pyridinium chlorochromate in dichloromethane T=20°C; 3 h; Inert atmosphere; optical yield given as percent ee;

toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid in dichloromethane T=4°C; Baeyer-Villiger oxidation; 48 h;

sodium hydroxide; hydrogen; [RhCl(η2:η2-cycloocta-1,5-diene)]2 in methanol T=50°C; P=9000.9 Torr; 24 h; Title compound not separated from byproducts.;

toluene-4-sulfonic acid in toluene 4 h; Heating / reflux;

1: With [Pd(S,S-chiraphos)(PhCN)2](SbF6)2; water in acetone T=10°C; 24 h; Inert atmosphere; 2: With bis(trimethylsilyl)-peroxide; tin(IV) chloride in n-heptane; dichloromethane T=0 - 20°C; Inert atmosphere; optical yield given as percent eeenantioselective reaction;

1.1: triphenylphosphine; lithium hydroxide hydrate; lithium chloride / water / |Reflux 2.1: calcium carbonate; palladium diacetate / methanol / 4 h / 60 °C 2.2: 20 °C 3.1: copper diacetate; DEMS; josiphos / tetrahydrofuran; toluene; tert-butyl alcohol / 3 h / 20 °C / |Inert atmosphere 4.1: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / |Inert atmosphere View Scheme