Multi-step reaction with 8 steps
1.1: 89 percent / imidazole / dimethylformamide / 1 h / 25 °C
2.1: 75 percent / H2 / Pd/C / methanol; tetrahydrofuran / 10 h / 50 °C / 760.05 Torr
3.1: 93 percent / PPh3; imidazole; I2 / 4-DMAP / acetonitrile; diethyl ether / 1 h / 25 °C
4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
4.2: 72 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 2.5 h / -78 - -30 °C
5.1: 89 percent / BF3*Et2O / CH2Cl2 / 1.5 h / 25 °C
6.1: 95 percent / NaBH4; NiCl2; H2 / ethylene diamine / ethanol / 1 h / 0 °C / 760.05 Torr
7.1: 99 percent / Et2Zn; DME; cyclo-(S,S)-(n-Bu)B-[OCH(CONMe2)]2 / CH2Cl2 / 6 h / 20 °C
8.1: 1.60 g / Ag2O; TBAI / toluene / 24 h / 25 - 50 °C
With
1H-imidazole; sodium tetrahydroborate; n-butyllithium; 1,2-dimethoxyethane; boron trifluoride diethyl etherate; hydrogen; iodine; diethylzinc; tetra-(n-butyl)ammonium iodide; triphenylphosphine; nickel dichloride; silver(l) oxide; (4S,5S)-2-butyl-N4,N4,N5,N5-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide;
dmap; palladium on activated charcoal; ethylenediamine;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
7.1: Charette cyclopropanation;
DOI:10.1021/ja011338b