Multi-step reaction with 12 steps
1: 94 percent / sodium borohydride / ethanol / 4 h / -15 °C
2: 93 percent / pyridine; 4-(dimethylamino)pyridine / 0 - 20 °C
3: 85 percent / dimethylsulfoxide / 3 h / 20 °C
4: 95 percent / pTSA / benzene / 5 h / Heating
5: 91 percent / diisobutylaluminum hydride / toluene / 1 h / 0 °C
6: 96 percent / sodium borohydride / ethanol / 1.5 h / -20 °C
7: 95 percent / HCl / acetone / 2 h / 20 °C
8: 99 percent / imidazole / dimethylformamide / 0 - 20 °C
9: toluene / 31 h / 138 °C
10: 80 percent / sodium periodate; RuCl3 / H2O; CCl4; acetonitrile / 7 h / 20 °C
11: 81 percent / N,N'-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 20 °C
12: triethylsilane; Pd(OAc)2; molecular sieves 4 Angstroem / acetone / 20 °C
With
pyridine; 1H-imidazole; hydrogenchloride; triethylsilane; dmap; ruthenium trichloride; palladium diacetate; sodium tetrahydroborate; sodium periodate; 4 A molecular sieve; diisobutylaluminium hydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide;
In
tetrachloromethane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1021/ol027125o