Multi-step reaction with 7 steps
1: 74 percent / DIBAL / tetrahydrofuran; toluene / 3 h / -78 °C
2: 39 percent / imidazole / dimethylformamide; hexamethylphosphoric acid triamide / 1.33 h / 50 °C
3: 31 percent / potassium tert-butoxide / tetrahydrofuran / -78 °C / a) 15 min b) 5 h
4: 78 percent / CuI, Et3N / PdCl2(PPh3)2 / a) 50 deg C, 3 h b) room temp., overnight
5: 94 percent / NH4OH / methanol / 18 h / Ambient temperature
6: 97 percent / HOAc, tetrabutylammonium fluoride / tetrahydrofuran / 8.67 h / Ambient temperature
7: 86 percent / methyltriphenoxyphosphonium iodide / CH2Cl2 / 1. -78 deg C -> room temp. , 30 min 2. 2 h at room temp.
With
1H-imidazole; ammonium hydroxide; copper(l) iodide; potassium tert-butylate; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; diisobutylaluminium hydride; acetic acid; triethylamine;
bis-triphenylphosphine-palladium(II) chloride;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00297a034