Multi-step reaction with 11 steps
1: 78 percent / ethanol / 12 h / Heating
2: 1.) NaH / 1a.) toluene, 60 deg C, 30 min, 1b.) 100 deg C, 10 min, 2.) reflux
3: 92 percent / lithium aluminum hydride / tetrahydrofuran / 20 h / Heating
4: 87 percent / N-methylmorpholine N-oxide, tris(triphenylphosphine)ruthenium(II) dichloride / acetone / 20 h / Ambient temperature
6: 1.) LDA / 1.) THF, 0 deg C, 30 min, 2.) -90 deg C, 2 h
7: methanol / 3 h / Ambient temperature
8: 1.) LDA / 1.) THF, hexane, -70 deg C, 40 min, 2a.) 10 min, 2b.) -30 deg C, 1 h
9: 1.) triethylborane, 2.) sodium borohydride / 1.) THF, -70 deg C, 1 h, 2.) -70 deg C, 1.5 h
10: H2, triethylamine / 10percent Pd/C / methanol / 0.33 h / Ambient temperature
11: 99.8 percent / 1 N sodium hydroxide / ethanol / 20 h / Ambient temperature
With
sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; tris(triphenylphosphine)ruthenium(II) chloride; triethyl borane; hydrogen; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; acetone;
DOI:10.1021/jm00163a011