Multi-step reaction with 12 steps
1: 76 percent / aq. NaOH / tetrahydrofuran / 48 h / Heating
2: 93 percent / pyridine / 96 h / 20 °C
3: PBu3; NEt3; HCOOH / Pd(dba)2 / tetrahydrofuran / Heating
4: 67 percent / OsO4; NMMO / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 144 h / 20 °C
5: 61 percent / DIBALH / CH2Cl2; toluene / 0.5 h
6: 99 percent / sodium periodate / tetrahydrofuran; H2O / 72 h / 20 °C
7: 92 percent / imidazole / dimethylformamide / 5 h / 20 °C
8: 88 percent / NaBH4 / methanol / 0.33 h / 0 °C
9: 57 percent / n-butyllithium / tetrahydrofuran; hexane / 20 h / 20 °C
10: 48 percent / tert-butyl hydroperoxide; palladium(II) acetate / toluene / 72 h / 50 °C
11: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C
12: 71 percent / 4-pyrrolidinopyridine; dicyclohexyl carbodiimide / toluene; CH2Cl2 / 0.75 h / 20 °C
With
1H-imidazole; tert.-butylhydroperoxide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; formic acid; tributylphosphine; tetrabutyl ammonium fluoride; palladium diacetate; diisobutylaluminium hydride; 4-pyrrolidin-1-ylpyridine; 4-methylmorpholine N-oxide; triethylamine; dicyclohexyl-carbodiimide;
bis(dibenzylideneacetone)-palladium(0);
In
tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1002/1099-0690(200105)2001:9<1761::AID-EJOC1761>3.0.CO;2-O