potassium hydroxide; hydrazine in diethylene glycol T=20 - 185°C; Wolff-Kishner reduction;

1: 90 percent / trimethylsilyl chloride, NaI / acetonitrile / 1 h 2: 62 percent / hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 1) 120 deg C, 0.5 h, 2) 185 deg C, 1.5. h View Scheme

ethanol; sodium

1: 2) boron trifluoride etherate / 1) dirhodium tetraacetate / 1) CH2Cl2, 25 h, 2) RT, 1 h 2: NaBH4, CeCl3*7H2O / CH2Cl2; ethanol / 0.17 h 3: 70 percent / para-methylated variant of Martin reagent / CH2Cl2 / 1) -100 deg C, 6 h, 2) warm to RT, 3) RT, 12 h 4: 86 percent / KOH / methanol; H2O / 12 h / Ambient temperature View Scheme