Multi-step reaction with 10 steps
1.1: 97 percent / imidazole / dimethylformamide / 12 h / 20 °C
2.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / 0 °C
2.2: 95 percent / tetrahydrofuran; pentane / -70 - 20 °C
3.1: dimethyl dioxirane / CH2Cl2 / 0.5 h / -65 °C
3.2: 90 percent / CH2Cl2 / 0.25 h / -65 °C
4.1: 95 percent / NaH / hexamethylphosphoric acid triamide / 0.5 h / 0 °C
5.1: 86 percent / i-Pr2NEt / CH2Cl2 / 3 h / -65 - 20 °C
6.1: 93 percent / DCC; DMAP / CH2Cl2 / 14 h / 20 °C
7.1: 100 percent / glacial AcOH / methanol; H2O / 6 h / 0 °C
8.1: NaH / 4 h / 20 °C
8.2: 86 percent / 48 h / 20 °C
9.1: 19.4 mg / n-Bu3SnH; AIBN / toluene / 2 h / 110 °C
10.1: 100 percent / TiCl4; TMEDA; Zn / PbCl2 / tetrahydrofuran; CH2Cl2 / 2 h / Heating
With
1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; titanium tetrachloride; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; zinc;
lead(II) chloride;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide; toluene; pentane;
DOI:10.1021/ol034100w