Multi-step reaction with 12 steps
1.1: i-PrMgCl / tetrahydrofuran / 1 h / 0 °C
1.2: 88 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C
2.1: CuI / tetrahydrofuran; diethyl ether / 0.67 h / 0 °C
2.2: tetrahydrofuran; diethyl ether / -78 °C
2.3: 100 percent / tetrahydrofuran; diethyl ether / 4 h / -78 °C
3.1: 99 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C
4.1: 76 percent / imidazole / dimethylformamide / 24 h / 20 °C
5.1: 83 percent / molecular sieves 4 Angstroem; NMO; TPAP / CH2Cl2 / 0.5 h / 20 °C
6.1: 69 percent / Huenig base / CH2Cl2 / 5 h / -78 - 0 °C
7.1: (R,R)-2,6-bis(4-(4-EtO-C6H4)-4,5-H2-1,3-oxazol-2-yl)pyridine; FeBr3; AgSbF6 / molecular sieves 5 Angstroem / CH2Cl2 / 0.25 h / 20 °C
7.2: CH2Cl2 / 30 h / -70 °C
8.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C
8.2: tetrahydrofuran / 0.5 h / 0 °C
9.1: LiAlH4 / tetrahydrofuran / 0.17 h / 0 °C
10.1: Huenig base; TBAI / 1,2-dichloro-ethane / 2 h / 20 °C
11.1: AcOH; TBAF / tetrahydrofuran / 24 h / 20 °C
11.2: imidazole / dimethylformamide / 22 h / 0 - 20 °C
12.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.83 h / -20 °C
12.2: tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -20 °C
With
1H-imidazole; silver hexafluoroantimonate; copper(l) iodide; ferric(III) bromide; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; isopropylmagnesium chloride; tetra-(n-butyl)ammonium iodide; acetic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; (R,R)-2,6-bis(4-(4-EtO-C6H4)-4,5-H2-1,3-oxazol-2-yl)pyridine;
5A molecular sieve;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
7.2: enantioselective Diels-Alder reaction;