1: 1.) LiN(i-Pr)2 / 1.) HMPTA, THF, -75 deg C, 1 h, 2.) HMPTA, THF, 0.5 h 2: 1.) lithium bistrimethylsilylamide / 1.) HMPTA, THF, from -75 to -70 deg C, 1.5 h, 2.) HMPTA, THF, from -75 to -70 deg C, 1 h 3: 95 percent / diisobutylaluminium hydride / hexane / 1 h / -75 °C 4: 100 percent / Amberlite IRA-400 / methanol / 24 h / Ambient temperature 5: 97 percent / H2 / Lindlar's catalyst / hexane View Scheme

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toluene-4-sulfonic acid T=85°C; 18 h;

toluene-4-sulfonic acid in benzene Heating;

in diethyl ether; toluene

1: H2 / Ni 2: TsOH View Scheme

1: (i) CH3CO3H, Na2CO3, (ii) H2O, (iii) CrO3, aq. H2SO4 2: H2 / Ni 3: TsOH View Scheme

1: 83 percent / lithium diisopropylamide / tetrahydrofuran / -80 °C 2: 90 percent / 1 N aq. HCl / 2 h / 50 °C 3: FClO3, KHCO3 / methanol / 20 °C 4: 36 percent / tri-sec-butylborohydride (K Selectride) / tetrahydrofuran 5: 1.) O3, 2.) (CH3)2S / 1.) MeOH, -70 deg C View Scheme

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