Multi-step reaction with 8 steps
1: 1.) potassium dihydrogen phosphate, SeO2, 2.) pyridinium dichromate, MgSO4 / 1.) toluene, reflux, 2 h, 2.) CH2Cl2, RT, 3.5 h
2: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to RT
3: Oxone / methanol / 12 h / Ambient temperature
4: 1.) copper(I) iodide, 2.) Me3SiCl / 1.) THF, -20 deg C, 10 min, 2.) THF, from -78 deg C to RT, 1 h
5: 1.) CeCl3*7H2O, 2.) NaBH4 / 1.) MeOH, RT, 10 min, 2.) MeOH, 0 deg C
6: 72 percent / collidine / CH2Cl2 / 0.08 h / 0 °C
7: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, a) from -78 deg C to RT, 12 h, b) 40 deg C, 24 h
8: collidine / CH2Cl2 / 8 h / Ambient temperature
With
2,3,5-trimethyl-pyridine; Oxone; sodium tetrahydroborate; potassium dihydrogenphosphate; copper(l) iodide; dipyridinium dichromate; chloro-trimethyl-silane; selenium(IV) oxide; cerium(III) chloride; dimethylsulfide; magnesium sulfate; ozone; lithium diisopropyl amide;
In
methanol; dichloromethane;
DOI:10.1139/v97-146