1.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 0 - 20 °C / |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C / |Inert atmosphere 2.2: 2 h / -78 - 20 °C / |Inert atmosphere 3.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / dichloromethane / 48 h / 20 °C / |Inert atmosphere 4.1: hydrogenchloride / methanol; water / 0 °C / |Inert atmosphere 5.1: sodium carbonate / ethanol / 24 h / 85 °C / |Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 7.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / |Inert atmosphere 7.2: 1 h / -78 °C / |Inert atmosphere View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C / |Inert atmosphere 1.2: 2 h / -78 - 20 °C / |Inert atmosphere 2.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / dichloromethane / 48 h / 20 °C / |Inert atmosphere 3.1: hydrogenchloride / methanol; water / 0 °C / |Inert atmosphere 4.1: sodium carbonate / ethanol / 24 h / 85 °C / |Inert atmosphere 5.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 6.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / |Inert atmosphere 6.2: 1 h / -78 °C / |Inert atmosphere View Scheme

1.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / dichloromethane / 48 h / 20 °C / |Inert atmosphere 2.1: hydrogenchloride / methanol; water / 0 °C / |Inert atmosphere 3.1: sodium carbonate / ethanol / 24 h / 85 °C / |Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 5.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / |Inert atmosphere 5.2: 1 h / -78 °C / |Inert atmosphere View Scheme

1.1: hydrogenchloride / methanol; water / 0 °C / |Inert atmosphere 2.1: sodium carbonate / ethanol / 24 h / 85 °C / |Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / |Inert atmosphere 4.2: 1 h / -78 °C / |Inert atmosphere View Scheme

1.1: sodium carbonate / ethanol / 24 h / 85 °C / |Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / |Inert atmosphere 3.2: 1 h / -78 °C / |Inert atmosphere View Scheme

1.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / |Inert atmosphere 2.2: 1 h / -78 °C / |Inert atmosphere View Scheme

iron(II) sulfate 0.25 h; Heating;

in xylene T=205°C;

chemical stability of title compound in fresh culture medium in the presence of the producing and non-producing cell lines of Tabernaemontana divaricata; Product distribution;

chemical stability of title compound in fresh culture medium in the presence of the producing and non-producing cell lines of Tabernaemontana divaricata; Product distribution;