1: 1.) 1-chloro-3,5-diphenylboracyclopentane, EtN(i-Pr) 2: H2 View Scheme

2: 1) hydrogen, 2)hydrogen / 1) Raney-Ni, 2) Pd/C View Scheme

2: 1) hydrogen, 2)hydrogen / 1) Raney-Ni, 2) Pd/C View Scheme

1: hydrogen; palladium(II) oxide hydrate / benzene / 5 h / 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere View Scheme

1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: hydrogen; palladium(II) oxide hydrate / benzene / 5 h / 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere View Scheme

1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; toluene / 20 °C 2.1: sodium periodate / tetrahydrofuran; water / 1 h 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 3.2: 4 h / -78 - 20 °C 4.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 5.1: hydrogen; palladium(II) oxide hydrate / benzene / 5 h / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere View Scheme

1.1: 1H-imidazole / dichloromethane / 2 h / 0 °C / Inert atmosphere 2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; toluene / 20 °C 3.1: sodium periodate / tetrahydrofuran; water / 1 h 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 4.2: 4 h / -78 - 20 °C 5.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: hydrogen; palladium(II) oxide hydrate / benzene / 5 h / 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 4 h / -78 - 20 °C 2.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 3.1: hydrogen; palladium(II) oxide hydrate / benzene / 5 h / 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 4 h / -78 - 20 °C 2.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 3.1: hydrogen; palladium(II) oxide hydrate / benzene / 5 h / 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere View Scheme

1: 1.) 1-chloro-3,5-diphenylboracyclopentane, EtN(i-Pr) 2: H2 View Scheme