1: sodium iodide / acetone / 8 h / Heating 2: potassium carbonate / acetonitrile / 10 h / Heating 3: 2.) n-BuLi / tetrahydrofuran / 0.5 h / -78 - -30 °C / 1.) acetonitrile, reflux, 10 h; 2.) THF, from -78 deg C to -30 deg C, 30 min 4: hexamethylphosphoric acid triamide / 1.) -78 deg C, 30 min; 2.) from -78 deg C to 0 deg C, 90 min 5: 1.) Jones oxidation, 0 deg C; 2.) saponification View Scheme

1: potassium carbonate / acetonitrile / 10 h / Heating 2: 2.) n-BuLi / tetrahydrofuran / 0.5 h / -78 - -30 °C / 1.) acetonitrile, reflux, 10 h; 2.) THF, from -78 deg C to -30 deg C, 30 min 3: hexamethylphosphoric acid triamide / 1.) -78 deg C, 30 min; 2.) from -78 deg C to 0 deg C, 90 min 4: 1.) Jones oxidation, 0 deg C; 2.) saponification View Scheme

1: 2.) n-BuLi / tetrahydrofuran / 0.5 h / -78 - -30 °C / 1.) acetonitrile, reflux, 10 h; 2.) THF, from -78 deg C to -30 deg C, 30 min 2: hexamethylphosphoric acid triamide / 1.) -78 deg C, 30 min; 2.) from -78 deg C to 0 deg C, 90 min 3: 1.) Jones oxidation, 0 deg C; 2.) saponification View Scheme

1: lead tetraacetate / CH2Cl2 / 1.) -20 deg C, 15 min, 2.) from -20 to 0 deg C, 15 min 2: hexamethylphosphoric acid triamide / 1.) -78 deg C, 30 min; 2.) from -78 deg C to 0 deg C, 90 min 3: 1.) Jones oxidation, 0 deg C; 2.) saponification View Scheme

1: 10 percent perchloric acid / tetrahydrofuran / 24 h / 0 °C 2: lead tetraacetate / CH2Cl2 / 1.) -20 deg C, 15 min, 2.) from -20 to 0 deg C, 15 min 3: hexamethylphosphoric acid triamide / 1.) -78 deg C, 30 min; 2.) from -78 deg C to 0 deg C, 90 min 4: 1.) Jones oxidation, 0 deg C; 2.) saponification View Scheme

1: hexamethylphosphoric acid triamide / 1.) -78 deg C, 30 min; 2.) from -78 deg C to 0 deg C, 90 min 2: 1.) Jones oxidation, 0 deg C; 2.) saponification View Scheme

1: hexamethylphosphoric acid triamide / 1.) -78 deg C, 30 min; 2.) from -78 deg C to 0 deg C, 90 min 2: 1.) Jones oxidation, 0 deg C; 2.) saponification View Scheme

1.) Jones oxidation, 0 deg C; 2.) saponification; Multistep reaction;