Multi-step reaction with 11 steps
1: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 2.) MeOH, CH2Cl2, from -78 deg C to RT, overnight
2: pyridine / 24 h / Ambient temperature
3: Ac2O, HNO3, H2SO4 / 0.67 h / -12 °C
4: 1M aq. NaOH / dioxane / 144 h / Ambient temperature
5: 1.) aq. CsHCO3 / 1.) MeOH, 2.) DMF, 57 deg C, 18 h
6: pyridinium chlorochromate / CH2Cl2 / 4 h / Ambient temperature
7: 72 h / Ambient temperature
8: SnCl2 / 18 h / Heating
9: H2 / 5 percent Pd/C / methanol / 3 h / 2585.74 Torr / Ambient temperature
10: SOCl2 / 0.25 h / Heating
11: pyridine / 4 h / Ambient temperature
With
pyridine; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; cesium bicarbonate; sulfuric acid; hydrogen; nitric acid; acetic anhydride; ozone; pyridinium chlorochromate; tin(ll) chloride;
palladium on activated charcoal;
In
1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/jm980166z