1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 10 °C / Inert atmosphere 1.2: 1.5 h / 0 - 10 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 15 h / 70 °C / Inert atmosphere 3.1: Reduced nicotinamide-adenine dinucleotide; NADPH; Lycopersicon esculentum 12-oxophytodienoate reductase / dimethyl sulfoxide / 22 h / 30 °C / pH 7 / Enzymatic reaction; Aqueous phosphate buffer 4.1: potassium hydroxide; water / 6 h / 25 °C 5.1: hydrogen / Raney Nickel / water / 30 °C 6.1: acetic acid / ethanol / 35 °C / pH 7.5 View Scheme

1 h; Heating;

(i) Al(OiPr)3, Al(OsBu)3, (ii) (pyrolysis); Multistep reaction;

1: With lithium hexamethyldisilazane in tetrahydrofuran T=-78°C; 0.75 h; Inert atmosphere; 2: With trifluoromethylsulfonic anhydride in tetrahydrofuran T=-78 - 20°C; Inert atmosphere; 3: With ammonium chloride in tetrahydrofuran; water T=20°C;

sodium ethanolate in ethanol T=20 - 50°C;

(i) KOH, (ii) NaNO2, aq. H2SO4, (iii) (decarboxylation); Multistep reaction;

ytterbium trichloride in ethanol T=20°C; 24 h;

1 h; Heating;

1.1: tetreamethyl ammonium hydroxide / hexane; water / 0.08 h / 5 - 10 °C 1.2: 0.17 h / 5 - 15 °C 2.1: Pd0(tris(tert-butyl)phosphine)2; water; sodium carbonate / toluene / 12 h / 50 °C / Inert atmosphere View Scheme