1: KOH / H2O; dioxane / Heating 2: H2 3: 81 percent / PPA 4: 90 percent 5: LAH / tetrahydrofuran / Heating 7: 93 percent / 33percent aq. KOH 8: 74 percent 9: 95 percent / toluene; acetonitrile / 24 h / 120 °C 10: 2.2M BH3*THF / 5 h / Heating View Scheme

1: 2.) (COOH)2*H2O, trimethyl orthoformate / 1.) dioxane, reflux, 12 h; 2.) dioxane, reflux, 2 h 2: 98 percent / H2 / Pt-C / methanol 3: 1.) acetyl chloride; 2.) ZnCl2 / 1.) CH2Cl2, r.t., overnight; 2.) THF, reflux, 6 h 4: H2 / 3percent Pt-C / acetic acid / 18 h / Ambient temperature View Scheme