Me2AlTeMe in toluene T=23°C; 10 h;

selenium

1.1: selenium(IV) oxide; ethanol / 2 h / |Inert atmosphere; |Reflux 2.1: manganese(IV) oxide; sodium carbonate / dichloromethane / 23 °C / |Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 23 °C / |Inert atmosphere 3.2: 24 h / 0 °C / |Inert atmosphere 4.1: magnesium; dilithium tetrachlorocuprate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 5.1: o,o'-dichloro-BINOL; antimony(V) pentachloride / dichloromethane / 0.25 h / -78 °C / |Inert atmosphere 6.1: water; potassium permanganate; sodium periodate; sodium carbonate / tert-butyl alcohol / 12 h / 23 °C / |Inert atmosphere View Scheme

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 23 °C / |Inert atmosphere 1.2: 24 h / 0 °C / |Inert atmosphere 2.1: magnesium; dilithium tetrachlorocuprate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 3.1: o,o'-dichloro-BINOL; antimony(V) pentachloride / dichloromethane / 0.25 h / -78 °C / |Inert atmosphere 4.1: water; potassium permanganate; sodium periodate; sodium carbonate / tert-butyl alcohol / 12 h / 23 °C / |Inert atmosphere View Scheme

1.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / |Inert atmosphere; |Reflux 1.2: 1 h / |Inert atmosphere 2.1: phosphorus tribromide / tetrahydrofuran / 0 °C / |Inert atmosphere 3.1: magnesium; dilithium tetrachlorocuprate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 4.1: o,o'-dichloro-BINOL; antimony(V) pentachloride / dichloromethane / 0.25 h / -78 °C / |Inert atmosphere 5.1: water; potassium permanganate; sodium periodate; sodium carbonate / tert-butyl alcohol / 12 h / 23 °C / |Inert atmosphere View Scheme

1: phosphorus tribromide / tetrahydrofuran / 0 °C / |Inert atmosphere 2: magnesium; dilithium tetrachlorocuprate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 3: o,o'-dichloro-BINOL; antimony(V) pentachloride / dichloromethane / 0.25 h / -78 °C / |Inert atmosphere 4: water; potassium permanganate; sodium periodate; sodium carbonate / tert-butyl alcohol / 12 h / 23 °C / |Inert atmosphere View Scheme

1.1: manganese(IV) oxide; sodium carbonate / dichloromethane / 23 °C / |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 23 °C / |Inert atmosphere 2.2: 24 h / 0 °C / |Inert atmosphere 3.1: magnesium; dilithium tetrachlorocuprate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 4.1: o,o'-dichloro-BINOL; antimony(V) pentachloride / dichloromethane / 0.25 h / -78 °C / |Inert atmosphere 5.1: water; potassium permanganate; sodium periodate; sodium carbonate / tert-butyl alcohol / 12 h / 23 °C / |Inert atmosphere View Scheme

pyridine T=60°C;

tetrachloromethane; N-bromosuccinmide; barium carbonate Erhitzen des Reaktionsprodukts mit Natriumacetat und Essigsaeure und Erwaermen des erhaltenen 13-Isopropyl-podocarpatrien-(8.11.13)-saeure-(15)-methylesters mit methanol. Kalilauge;

ammonium cerium(IV) nitrate; sodium acetate; acetic acid 1.) reflux, 10 h, 2.) CH2Cl2, 3 h; Yield given. Multistep reaction. Yields of byproduct given;