1: (i) OsO4, Py, benzene, (ii) D-mannitol, aq. NaOH, CH2Cl2 2: Et2NSF3 / CH2Cl2 View Scheme

1.1: sodium t-butanolate / 1-methyl-pyrrolidin-2-one; tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere 1.2: 3 h / 0 - 20 °C / |Inert atmosphere 2.1: diisobutylaluminium hydride / toluene / 1.5 h / -78 °C / |Inert atmosphere 3.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -95 °C / |Inert atmosphere 3.2: -95 - -30 °C / |Inert atmosphere 3.3: 1.5 h / -30 - 0 °C / |Inert atmosphere 4.1: zinc / N,N-dimethyl-formamide / 2 h / 20 °C / |Inert atmosphere 5.1: indium tribromide / 1,2-dichloro-ethane / 0.5 h / 20 °C / |Inert atmosphere; |Glovebox 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,2-dichloro-ethane / 1.5 h / |Inert atmosphere; |Reflux; |Glovebox View Scheme

Multistep reaction;