Multi-step reaction with 11 steps
1: 85 percent / n-BuLi / tetrahydrofuran
2: 95 percent / NaBH4 / methanol
3: 95 percent / 4-(dimethylamino)pyridine / CH2Cl2
4: 1.) n-BuLi, 2.) B(OMe)3, 3.) H2O2, HOAc
5: diethyl azodicarboxylate, Ph3P / tetrahydrofuran
6: 95 percent / Bu4NF / tetrahydrofuran
7: 85 percent / CBr4, Ph3P / diethyl ether
8: 90 percent / dimethylformamide
9: 75 percent / conc. HCl, HOAc
10: EDC, HOBT, i-Pr2NEt / dimethylformamide
11: 95 percent / HCl (gas) / ethyl acetate
With
hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; Trimethyl borate; carbon tetrabromide; tetrabutyl ammonium fluoride; dihydrogen peroxide; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(99)00181-X