Multi-step reaction with 5 steps
1: 83 percent / lithium aluminum hydride / tetrahydrofuran / 1.) -70 deg C, 75 min, 2.) 3 h
2: 62 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 1.) 0 deg C, 45 min, 2.) room temperature, 30 min
3: 1.) ozone, 2.) sodium borohydride / methanol / 1.) -78 deg C, 43 min
4: 1.) o-nitrophenyl selenocyanate, tri-n-butylphosphine, 2.) aq. hydrogen peroxide / 1.) THF, 0 deg C, 15 min; room temperature, 45 min, 2.) 0 deg C, 20 min; 30 min
5: 80 percent / diisobutylaluminum hydride / toluene / -70 - -65 °C
With
sodium tetrahydroborate; lithium aluminium tetrahydride; ortho-nitrophenyl selenocyanate; tributylphosphine; dihydrogen peroxide; diisobutylaluminium hydride; ozone; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; toluene;
DOI:10.1021/ja00343a030