1: aq. HBr / acetic acid 2: Na, liq. NH3 View Scheme

1: (phenylsulfonyl)methane With n-butyllithium in tetrahydrofuran; hexane T=-78°C; Metallation; 0.5 h; 2: 6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one With benzoyl chloride in tetrahydrofuran; hexane T=-78 - 20°C; Addition; acylation; 3 h; 3: With potassium tert-butylate in tetrahydrofuran; hexane Elimination; aromatization; 3 h; Heating;

mixture of spironaphthalenones in 1,3,5-trimethyl-benzene 0.5 h; Heating;

(hydroxy(tosyloxy)iodo)benzene in acetonitrile T=20°C; 0.25 h; Molecular sieveInert atmosphere;

sulfur T=200 - 220°C;

sulfur

(i) LiAlH4, (ii) Se; Multistep reaction;

2: (i) LiAlH4, (ii) Se View Scheme

(i), (ii) Pd-C; Multistep reaction;

hydrogen bromide; acetic acid