pyridine in dichloromethane T=0 - 20°C; 12 h;

water; dihydrogen peroxide T=90°C; 12 h; Yields of byproduct given;

triphenylphosphine in dichloromethane T=20°C;

1: (5R)-6,7-dihydro-3,9,10,11-tetramethoxy-5H-dibenzo[a,c]cyclohepten-5-ol With Zn(N3)2/bis-pyridine complex; di-isopropyl azodicarboxylate; triphenylphosphine in toluene 4 h; Inert atmosphere; 2: With hydrogen in ethanol 20 h; Inert atmosphere; 3: acetic anhydride With pyridine in dichloromethane T=0 - 20°C; 12 h; Inert atmosphere; optical yield given as percent ee;

1.1: triethylsilane; bis(trimethylsilyl)-acetylene / 1,2-dichloro-ethane / 6 h / 65 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: borane-THF / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.2: 4.5 h / 20 - 40 °C / Inert atmosphere 3.1: oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / -78 - 20 °C / Inert atmosphere 4.1: lithium borohydride; (L)-TarB-NO2 / tetrahydrofuran / 0.58 h / Inert atmosphere 5.1: Zn(N3)2/bis-pyridine complex; di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 4 h / Inert atmosphere 5.2: Lindlar catalyst / 20 h / Inert atmosphere 5.3: 12 h / 0 - 20 °C / Inert atmosphere View Scheme

1.1: borane-THF / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 1.2: 4.5 h / 20 - 40 °C / Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / -78 - 20 °C / Inert atmosphere 3.1: lithium borohydride; (L)-TarB-NO2 / tetrahydrofuran / 0.58 h / Inert atmosphere 4.1: Zn(N3)2/bis-pyridine complex; di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 4 h / Inert atmosphere 4.2: Lindlar catalyst / 20 h / Inert atmosphere 4.3: 12 h / 0 - 20 °C / Inert atmosphere View Scheme

1.1: lithium borohydride; (L)-TarB-NO2 / tetrahydrofuran / 0.58 h / Inert atmosphere 2.1: Zn(N3)2/bis-pyridine complex; di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 4 h / Inert atmosphere 2.2: Lindlar catalyst / 20 h / Inert atmosphere 2.3: 12 h / 0 - 20 °C / Inert atmosphere View Scheme

1,1-diethoxyethylene; ozone 1) ether, -116 deg C, 2) ether, CH2Cl2, to r.t.; Yield given. Multistep reaction;

diethyl ether

1,1-diethoxyethylene; ozone 1) ether, -116 deg C, 2) ether, CH2Cl2, to r.t.; Yield given. Multistep reaction;