Multi-step reaction with 7 steps
1: 81 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C
2: 75 percent / MnO2 / CH2Cl2 / 1 h / Ambient temperature
3: 1.) lithium dicyclohexylamide / 1.) THF, hexane, 3 deg C, 2.) THF, hexane, -40 deg C
4: NaOMe / Ambient temperature
5: 1.) n-butyllithium, diisopropylamine / 1.) cyclohexane, hexane, 3 deg C, 2.) cyclohexane, hexane, THF, 3 deg C
6: 1.) methoxydiethylborane, 2.) sodium borohydride / 1.) THF, methanol, -75 deg C, 2.) THF, methanol, -75 deg C,
7: aq. NaOH / tetrahydrofuran
With
manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; diethyl methoxy borane; sodium methylate; diisobutylaluminium hydride; lithium dicyclohexylamide; diisopropylamine;
In
tetrahydrofuran; dichloromethane;
DOI:10.1021/jm00075a020