Multi-step reaction with 14 steps
1.1: 39.0 g / sodium methoxide / methanol / 2 h / Heating
2.1: LDA / tetrahydrofuran; hexane / 1 h / 0 °C
2.2: 80 percent / tetrahydrofuran; hexane / 1 h / 20 °C
3.1: 43 percent / p-toluenesulfonic acid monohydrate; triethyl orthoformate / CH2Cl2 / 19 h / 25 °C
4.1: 77 percent / potassium bis(trimethylsilyl)amide / diethyl ether; toluene / 2 h / 20 °C
5.1: 80 percent / aq. AcOH / 4 h / Heating
6.1: 97 percent / L-selectride / tetrahydrofuran / 17 h / 0 °C
7.1: diphenylphosphoryl azide; diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 17 h / 20 °C
8.1: LiAlH4 / ethanol; diethyl ether / 2 h / 20 °C
9.1: 528 mg / Et3N; DMAP / CH2Cl2 / 17 h / 20 °C
10.1: 83 percent / sodium hydroxide; tetrabutylammonium bromide / toluene; H2O / 0.67 h / 100 °C
11.1: 85 percent / O3; triphenylphosphine / CH2Cl2 / 9 h / -78 - 20 °C
12.1: 92 percent / potassium carbonate; tetrabutylammonium bromide / toluene / 2 h / Heating
13.1: 92 percent / sodium borohydride / ethanol / 1 h / 0 °C
14.1: 70 percent / boron tribromide / CH2Cl2 / 1 h / -40 °C
With
dmap; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; diphenylphosphoranyl azide; tetrabutylammomium bromide; sodium methylate; boron tribromide; potassium hexamethylsilazane; L-Selectride; potassium carbonate; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; orthoformic acid triethyl ester; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; toluene;
7.1: Mitsunobu coupling;
DOI:10.1021/ja027882h