Multi-step reaction with 7 steps
1.1: 1,4-bis-(9-O-dihydroquinidinyl)phthalazine; K3[Fe(CN)6]; K2OsO4*2H2O / K2CO3; CH3SO2NH2 / 2-methyl-propan-2-ol / 0 °C
1.2: 8.732 g / p-TsOH*H2O / acetone / 20 °C
2.1: 72 percent / Me3SiCl / diethyl ether; hexane / 6 h / -78 °C
3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
3.2: 59 percent / oxodiperoxymolybdenum(pyridine)-hexamethylphosphorictriamide / tetrahydrofuran / 3 h / -78 °C
4.1: NaH / 1,2-dimethoxy-ethane
4.2: 89 percent / 1,2-dimethoxy-ethane / 2 h / 20 - 60 °C
5.1: 98 percent / LiAlH4 / tetrahydrofuran / 5 - 20 °C
6.1: 91 percent / DABCO / CH2Cl2 / 0 - 20 °C
7.1: 98 percent / NaHCO3 / dimethylsulfoxide / 43 h / 60 - 80 °C
With
1,4-diaza-bicyclo[2.2.2]octane; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; potassium osmate(VI); lithium aluminium tetrahydride; chloro-trimethyl-silane; sodium hydride; sodium hydrogencarbonate; potassium hexacyanoferrate(III); lithium diisopropyl amide;
methanesulfonamide; potassium carbonate;
In
tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; tert-butyl alcohol;
DOI:10.1002/chem.200500282