Multi-step reaction with 11 steps
1: NaBH3CN / 2 h / 0 °C
2: 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
3: 78 percent / Bu3SnH, AIBN / toluene / 2 h / 80 °C
4: 88 percent / DIBAH / CH2Cl2 / 0.5 h / -65 °C
5: n-BuLi, (Me3Si)2NH / tetrahydrofuran; hexane / -65 °C
6: 84 percent / MeONa / tetrahydrofuran; methanol / 0.17 h / -20 °C
7: 66 percent / NaBH4 / methanol / 0.17 h / 0 °C
8: 91 percent / pyridine / 18 h / 20 °C
9: 77 percent / DIBAH / toluene / 0.5 h / -65 °C
10: 76 percent / Bu3P / tetrahydrofuran / 1 h / 50 °C
11: 78 percent / CsF / dimethylformamide / 24 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; 2,2'-azobis(isobutyronitrile); tributylphosphine; tri-n-butyl-tin hydride; sodium methylate; diisobutylaluminium hydride; sodium cyanoborohydride; cesium fluoride; 1,1,1,3,3,3-hexamethyl-disilazane;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00123a021