Multi-step reaction with 10 steps
1: 96 percent / conc. H2SO4 / 5 h / Heating
2: 65 percent / K2CO3, Bu4NI / acetone / 3 h / Heating
3: 1) NaH / 1) DMF, r.t., 0.5 h, 2) 90 deg C, 3 h
4: 95 percent / boron trifluoride etherate / CH2Cl2 / 0.5 h / Ambient temperature
5: 1) DIBALH, 2) 1N HCl / 1) a) CH2Cl2, -78 deg C, 0.5 h, 2) MeOH, 0 deg C, 0.5 h
6: 86 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 0 °C
7: CHCl3 / 5 h / Ambient temperature
8: methanol / 3 h
9: 90 percent / ethereal HCl / 5 h / Ambient temperature
10: lead tetraacetate / CH2Cl2; methanol / 0.08 h / 0 °C / 1) CH2Cl2, MeOH, 0 deg C, 5 min, 2) phosphate buffer pH 7, r.t., 0.5 h
With
lead(IV) acetate; hydrogenchloride; methanol; sulfuric acid; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; pyridinium chlorochromate;
In
methanol; dichloromethane; chloroform; acetone;
DOI:10.1021/jo00046a031