Multi-step reaction with 13 steps
1.1: 95 percent / Zn powder; Cu(OAc)2*H2O / acetic acid / 24 h / 80 - 90 °C
2.1: 87 percent / DBU / tetrahydrofuran / 20 °C
3.1: 96 percent / 2N HCl / 16 h / 20 °C
4.1: 89 percent / imidazole; DMAP / CH2Cl2; toluene / 16 h / 0 - 20 °C
5.1: CuI / 0 °C
5.2: 84 percent / diethyl ether / 1 h / 0 °C
6.1: 98 percent / LiBH4 / tetrahydrofuran / 0 - 20 °C
7.1: 83 percent / Bu3P / tetrahydrofuran / 16 h / 0 - 20 °C
8.1: Et3N / CH2Cl2 / 1 h / -10 °C
9.1: TBAF / tetrahydrofuran / 1 h / 0 - 5 °C
9.2: 812 mg / aq. NaOH / tetrahydrofuran / 0.75 h / 0 - 5 °C
10.1: n-BuLi; BF3*Et2O / tetrahydrofuran; hexane / 1.5 h / -78 °C
10.2: aq. TFA / 3 h / 20 °C
10.3: 88 percent / DBU / CH2Cl2 / 0.5 h / 0 - 5 °C
11.1: 100 percent / magnesium monoperoxophthalate hexahydrate / ethanol / 1.5 h / 20 °C
12.1: DIBALH / CH2Cl2 / 1 h / -78 °C
13.1: 1.107 g / PPTS / 20 °C
With
1H-imidazole; hydrogenchloride; dmap; copper(l) iodide; lithium borohydride; n-butyllithium; copper diacetate; magnesium bis(monoperoxyphthalate)hexahydrate; tributylphosphine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; acetic acid; toluene;
DOI:10.1021/jo026743f