Multi-step reaction with 10 steps
1.1: diisopropylamine / Pd(PPh3)4 / tetrahydrofuran / 0.33 h / 20 °C
1.2: 99 percent / CuI / tetrahydrofuran / 12 h
2.1: 99 percent / LAH / tetrahydrofuran / 20 h / Heating
3.1: 95 percent / imidazole / dimethylformamide / 0 - 20 °C
4.1: 72 percent / m-CPBA; NaOAc / CH2Cl2 / 6 h / 20 °C
5.1: 71 percent / CuI / tetrahydrofuran / 6 h / 20 °C
6.1: 40 percent / sodium hydride / dimethylformamide / 5 h / 20 °C
7.1: 89 percent / acetic acid / tetrahydrofuran; H2O
8.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 1 h / 20 °C
9.1: tert-butyllithium / tetrahydrofuran; pentane / 1.25 h / -78 - -20 °C
9.2: MgBr2 / diethyl ether; pentane; tetrahydrofuran / 0.25 h / -78 °C
10.1: 55 mg / DMAP / various solvent(s) / 5 h / 35 °C
With
1H-imidazole; dmap; lithium aluminium tetrahydride; tert.-butyl lithium; sodium acetate; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; diisopropylamine; 3-chloro-benzenecarboperoxoic acid;
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ja029139v