Multi-step reaction with 9 steps
1: 95 percent / dioxane / 21 h / 101 °C
2: 75 percent / CF3SO3H / CH2Cl2 / 13 h / 40 °C
3: NaBH4 / ethanol / 15 h / 25 °C
4: 83 percent / MnO2 / acetonitrile / 3 h / 82 °C
5: 1.) Bu2BOTf, i-Pr2NEt, / 1.) CH2Cl2, 0 deg C, 1 h, 2.) CH2Cl2, 0 deg C, 3 h
6: 93 percent / Bu3SnH, AIBN / benzene / 1 h / 80 °C
7: 52 percent / DEAD, hydrazoic acid, Ph3P / tetrahydrofuran / 16 h / 23 °C
8: 59 percent / NaOCH3 / 0.33 h / 0 °C
9: 82 percent / Ph3P, H2O, HOAc / tetrahydrofuran / 15 h / 25 °C
With
manganese(IV) oxide; sodium tetrahydroborate; hydrogen azide; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; water; tri-n-butyl-tin hydride; sodium methylate; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; acetonitrile; benzene;
DOI:10.1021/ja00092a012