Multi-step reaction with 16 steps
1.1: n-BuLi; 18-crown-6 / tetrahydrofuran; hexane / 1.17 h / -78 °C
1.2: 76 percent / tetrahydrofuran; hexane / 2.25 h / -78 °C
2.1: 87 percent / H2; ethylenediamine / P-2 Ni / ethanol
3.1: N,N-dimethylaniline / CH2Cl2 / 0.25 h / 0 °C
4.1: 516 mg / Et3N / CH2Cl2 / 0.42 h / 0 - 20 °C
5.1: Cu(TBS)2 / toluene / Heating
6.1: conc. HCl; triethylsilane / tetrahydrofuran / 6 h / 70 °C
7.1: 720 mg / Et3N / acetonitrile / 20 °C
8.1: 74 percent / DEAD; PPh3 / tetrahydrofuran / 3.5 h / 20 °C
9.1: CuBr*DMS / diethyl ether / 0 °C
9.2: 90 percent / diethyl ether; CH2Cl2 / 0.17 h / 0 - 20 °C
10.1: 66 percent / AlMe3 / CH2Cl2; toluene / 12 h / 20 °C
11.1: 99 percent / 2,6-lutidine / CH2Cl2 / 4 h / -78 °C
12.1: t-BuOK / diethyl ether / 2 h / 0 °C
13.1: 43 mg / t-BuOK; H2O / diethyl ether / 0 °C
14.1: 87 percent / HOBt; Et3N; EDC / dimethylformamide / -10 - 20 °C
15.1: aq. HCl / dioxane / 0.5 h / 20 °C
16.1: 60 percent / Et3N / tetrahydrofuran / 20 °C
With
2,6-dimethylpyridine; hydrogenchloride; triethylsilane; n-butyllithium; copper(I) bromide dimethylsulfide complex; 18-crown-6 ether; potassium tert-butylate; water; hydrogen; trimethylaluminum; benzotriazol-1-ol; N,N-dimethyl-aniline; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; ethylenediamine; triethylamine; triphenylphosphine; diethylazodicarboxylate;
Cu(TBS)2;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
8.1: Mitsunobu cyclization;
DOI:10.1021/jo001257i