1: 72 percent / DIBAL-H / toluene / -78 °C 2: 85 percent / KHMDS / tetrahydrofuran / -20 °C 3: Bu4NF / tetrahydrofuran / 23 °C View Scheme

1: 72 percent / DIBAL-H / toluene / -78 °C 2: 85 percent / KHMDS / tetrahydrofuran / -20 °C 3: Bu4NF / tetrahydrofuran / 23 °C 4: 82 percent / OsO4, (DHQD)2PYDZ / H2O; 2-methyl-propan-2-ol / 52 h / 0 °C 5: pyridine / CH2Cl2 / 23 °C 6: K2CO3 / methanol 7: n-BuLi / tetrahydrofuran / -20 °C View Scheme

With  lithium aluminium tetrahydride in  tetrahydrofuran  from 0 deg C to rt;  Yield given;