Multi-step reaction with 18 steps
1: 95 percent / dl-camphorsulfonic acid (CSA) / methanol / 20 °C
2: 93 percent / dl-camphorsulfonic acid (CSA)
3: 1.) LDA / 1.) THF, -78 deg C
4: 1.) diisobutylaluminium hydride, 2.) sodium borohydride / 1.) THF, -78 deg C
5: imidazole
6: i-Pr2NEt
7: lithium aluminium hydride
8: NaH
9: MgBr2 / diethyl ether / 20 °C
10: COCl2, Et3N / dimethylsulfoxide
11: 85 percent / tetrahydrofuran / -78 °C
12: Hg(OAc)2 / 48 h / 135 °C
13: 76 percent / tetrahydrofuran / -78 °C
14: Hg(OAc)2 / 48 h / 135 °C
15: NaBH4
16: Et3N
17: sodium iodide / acetone
18: 1.) t-BuLi / 1.) THF, -78 deg C, then 0 deg C
With
1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; camphor-10-sulfonic acid; mercury(II) diacetate; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; magnesium bromide; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; dimethyl sulfoxide; acetone;
DOI:10.1016/S0040-4039(01)93503-8