1: 3-(phenylsulfanyl)isobenzofuran-1(3H)-one With lithium tert-butylate in tetrahydrofuran T=-60°C; 0.416667 h; 2: 5-hydroxy-5,6,7,8-tetrahydro-naphthoquinone in tetrahydrofuran T=-60 - 20°C; Hauser annulation; Further stages.;

1: 58 percent / CHCl3 / 22 h / Heating 2: H2 / tris(triphenylphosphine)rhodium chloride / benzene / 14 h / 20 °C 3: 96 percent / sodium acetate / 0.5 h / 100 °C 4: 97 percent / H2 / tris(triphenylphosphine)rhodium chloride / benzene / 40 h / 20 °C 5: chromic anhydride / acetic acid; H2O / 24 h / 70 °C 6: 98 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 0.75 h / Heating 7: 78 percent / silver acetate / 0.25 h / Heating 8: aq. NH4OH / acetone / 24 h / 20 °C View Scheme

1: 98 percent / NaBH4 / methanol / 24 h / Heating 2: 58 percent / CHCl3 / 22 h / Heating 3: H2 / tris(triphenylphosphine)rhodium chloride / benzene / 14 h / 20 °C 4: 96 percent / sodium acetate / 0.5 h / 100 °C 5: 97 percent / H2 / tris(triphenylphosphine)rhodium chloride / benzene / 40 h / 20 °C 6: chromic anhydride / acetic acid; H2O / 24 h / 70 °C 7: 98 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 0.75 h / Heating 8: 78 percent / silver acetate / 0.25 h / Heating 9: aq. NH4OH / acetone / 24 h / 20 °C View Scheme

ammonium hydroxide in acetone T=20°C; 24 h;

1: 3.7 g / H2 / palladium-charcoal / benzene / 20 °C 2: 120 mg / silver(II) oxide, nitric acid / dioxane / 1 h / 20 °C 4: 98 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 0.75 h / Heating 5: 78 percent / silver acetate / 0.25 h / Heating 6: aq. NH4OH / acetone / 24 h / 20 °C View Scheme

1.1: NaBH4 1.2: ceric ammonium nitrate 2.1: LiOt-Bu / tetrahydrofuran / 0.42 h / -60 °C 2.2: 46 percent / tetrahydrofuran / -60 - 20 °C View Scheme

2: H2 / Pd 3: Na2CO3 View Scheme

1: H2 / Pd 2: Na2CO3 View Scheme

1: chromic anhydride / acetic acid; H2O / 24 h / 70 °C 2: 98 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 0.75 h / Heating 3: 78 percent / silver acetate / 0.25 h / Heating 4: aq. NH4OH / acetone / 24 h / 20 °C View Scheme

2: 98 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 0.75 h / Heating 3: 78 percent / silver acetate / 0.25 h / Heating 4: aq. NH4OH / acetone / 24 h / 20 °C View Scheme