Multi-step reaction with 9 steps
1: 97 percent / H2 / 10 percent Pd/C / ethanol
2: 90 percent / Et3N / dimethylformamide
3: 1.) pivaloyl chloride, 2.) BuLi / 1.) -70 deg C, 2.) THF
4: 69 percent / KHMDS, trisylazide / tetrahydrofuran
5: 96 percent / aq. LiOH, aq. H2O2 / tetrahydrofuran
6: 100 percent / TBTU, Et3N / CH2Cl2
7: 89 percent / H2 / 10 percent Pd/C / dimethylformamide
8: 90 percent / Et3N / dimethylformamide
9: DIBAL-H / CH2Cl2
With
lithium hydroxide; n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; pivaloyl chloride; potassium hexamethylsilazane; diisobutylaluminium hydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(99)00179-1