Yield given. Multistep reaction;

1: 1.) n-BuLi, 2.) CuI 2: 1.) NaH, 2.) n-BuLi / 1.) THF View Scheme

4-toluenesulfonyl azide; sodium hydride in tetrahydrofuran; benzene 6 h; temperature: 0 deg C to room temperature;

1: 1.) NaH, 2.) TosN3 / 1.) benzene, THF, 0 deg C, 1.5 h, 2.) benzene, THF, RT, 3 h 2: 58 percent / dirhodium(II) tetraacetate / CH2Cl2 / 2 h / Heating 3: 1.) O3, 2.) Me2S / 1.) MeOH, -70 deg C, 2.) MeOH, from -10 deg C to RT, 3 h 4: CrO3, aq. H2SO4 / acetone / 0.5 h 5: diethyl ether / 0.5 h / Ambient temperature 6: H20, phosphate buffer, α-chymotrypsin 7: 1.) NaH / 1.) THF, RT, 1.5 h, 2.) THF, 40 deg C, 1 h View Scheme