Multi-step reaction with 12 steps
1.1: 94 percent / NaH; TBAI / tetrahydrofuran; dimethylformamide / 12.5 h / 20 °C
2.1: 78 percent / TsOH*H2O / methanol / 18 h / 20 °C
3.1: 53 percent / NaH; triisopropylbenzylsulfonylimidazole / tetrahydrofuran; dimethylformamide / 0 - 20 °C
4.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / 20 °C
4.2: 72 percent / tetrahydrofuran; hexane / -20 - -10 °C
5.1: iodine; aq. NaHCO3 / acetonitrile / 0.83 h / 0 - 20 °C
6.1: Et2B(OMe); NaBH4 / tetrahydrofuran; methanol / 12 h / -78 °C
7.1: 6.02 g / para-toluenesulfonic acid monohydrate / acetone / 1 h / 0 °C
8.1: 75 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C
9.1: 85 percent / oxalyl chloride; DMSO; TEA / CH2Cl2 / -78 - 0 °C
10.1: i-PrMgCl / tetrahydrofuran / 1.5 h / 0 °C
10.2: 77 percent / tetrahydrofuran / 1 h / -10 °C
11.1: 90 percent / Dess-Martin periodinane / CH2Cl2 / 3.25 h / 20 °C
12.1: 81 percent / NaOMe / methanol; CH2Cl2 / -10 °C
With
sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; triisopropylbenzylsulfonylimidazole; TEA; diethyl methoxy borane; tetrabutyl ammonium fluoride; iodine; isopropylmagnesium chloride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/ol035849+