Multi-step reaction with 9 steps
1: 2.) AcOH, NaOAc / 1.) THF, 0 deg C, 1 h, 2.) H2O, steam bath, 30 min
2: 83 percent / H2 / 5percent Rh on alumina / ethanol
3: 100 percent / pyridine / CH2Cl2 / 2 h
4: 1.) LDA / 1.) DME, hexane, 60 min, 2.) 2 h
5: 100 percent / KOH / methanol / 3 h / Ambient temperature
6: 1.) 70percent HClO4, 2.) H2 / 2.) rhodium on alumina / 1.) EtOAc, 0 deg C, 75 min, 2.) 60 psi, 6 h
7: 80 percent / KOH / methanol; H2O / 18 h / 0 °C
8: 1.) LDA / 1.) DNE, pentane, -68 deg C, 2 h, 2.) 45 min
9: 1.) MeI, 2.) NaHCO3 / 1.) MeOH, 18 h, 2.) EtOAc, H2O
With
pyridine; potassium hydroxide; perchloric acid; hydrogen; sodium acetate; sodium hydrogencarbonate; acetic acid; lithium diisopropyl amide; methyl iodide;
Rh/Al2O3; rhodium on alumina;
In
methanol; ethanol; dichloromethane; water;
DOI:10.1021/ja00371a020