Multi-step reaction with 15 steps
1: lithium borohydride / tetrahydrofuran; methanol / 4 h / 0 °C
2: triethylamine / dichloromethane / 0.5 h / 20 °C
3: dimethyl sulfoxide / 4 h / 60 °C
4: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C
5: sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; sodium formate / water; tert-butyl alcohol / 2 h / 0 °C
6: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 5 h / 0 - 20 °C
7: diethyl ether / 0.08 h / -10 °C
8: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 6 h / 40 °C
9: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 - 20 °C
10: methanol; toluene-4-sulfonic acid / 2 h / 20 °C
11: oxalyl dichloride; dimethyl sulfoxide / 0.5 h / -78 °C
12: toluene / 4 h / 20 °C
13: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 3 h / 20 °C
14: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0 - 20 °C
15: hydrogenchloride / ethyl acetate / 3 h / 0 °C
With
2,6-dimethylpyridine; hydrogenchloride; methanol; lithium borohydride; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; oxalyl dichloride; lithium hydroxide monohydrate; dimethylsulfide borane complex; sodium formate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
11: Swern oxidation / 12: Wittig reaction;
DOI:10.1016/j.tetlet.2011.05.107