Multi-step reaction with 8 steps
1: TsOH / benzene
2: 1.) O3, 2.) DMS / 1.) MeOH, -78 deg C, 2.) rt
3: n-BuLi / tetrahydrofuran / 0 °C
4: 85 percent / n-BuLi / tetrahydrofuran / 0 °C
5: 78 percent / LiAlH4 / tetrahydrofuran / -78 - 0 °C
6: 1.) MsCl, Et3N, 2.) LiCl, HMPA / 1.) CH2Cl2, 0 deg C, 2.) rt
7: 99 percent / NaBH4 / methanol / Ambient temperature
8: 84 percent / imidazole / tetrahydrofuran / Ambient temperature
With
1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; 2,3-dimercapto-succinic acid; toluene-4-sulfonic acid; ozone; methanesulfonyl chloride; triethylamine; lithium chloride;
In
tetrahydrofuran; methanol; benzene;
DOI:10.1055/s-1997-3255