1: 89 percent / H2SO4 / methanol / Heating 2: 90 percent / LiAlH4 / tetrahydrofuran / 2 h / 25 °C 3: 87 percent / NEt3 / CH2Cl2 / 0 °C 4: 94 percent / trifluoroacetic acid / H2O / 1.5 h / 0 °C 5: 8.6 g / NaI / acetone / Heating 6: 3α,20β-hydroxysteroid dehydrogenase, K2HPO4 / ethanol / 24 h / 25 °C / other enzymes, other substrates, KM, Vmax; stereoselectivity 7: 86 percent / Ph3P, DEAD / tetrahydrofuran 8: 95 percent / 20percent aq. K2CO3 / methanol / 2 h / Ambient temperature 9: 1) MeOH, 80 deg C, overnight, 2) ether View Scheme