Multi-step reaction with 18 steps
1.1: 89 percent / p-toluenesulfonic acid / benzene / 2 h / Heating
2.1: H2; Pd-C; piperidine / 6 h / 20 °C / 7600.51 Torr
2.2: acetic acid / ethanol / 1.5 h / 15 °C
2.3: thionyl chloride; pyridine / CH2Cl2 / 1.5 h / 30 °C
3.1: 96 percent / diisobutylaluminum hydride / toluene / 2 h / -78 °C
4.1: 99 percent / sodium borohydride / H2O; tetrahydrofuran / 0.5 h / 0 °C
5.1: 100 percent / hydrochloric acid / H2O; methanol / 1 h / 20 °C
6.1: 37 percent / hydroquinone / 1,2-dichloro-benzene / 30 h / 20 - 170 °C
7.1: 96 percent / p-toluenesulfonic acid / benzene / 4 h / Heating
8.1: 77 percent / [Ir(cod)Pcy3(py)]+PF6- / CH2Cl2 / 48 h / -20 °C
9.1: 100 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 0 - 20 °C
10.1: o-nitrophenyl selenocyanate; tri-n-butylphosphine / tetrahydrofuran / 1 h / 20 °C
10.2: 95 percent / hydrogen peroxide / tetrahydrofuran; H2O / 2 h / 0 - 20 °C
11.1: ozone / CH2Cl2; methanol / -78 °C
11.2: 92 percent / triphenylphosphine / CH2Cl2; methanol / 0.5 h / -78 - 20 °C
12.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -40 °C
12.2: 97 percent / tetrahydrofuran; hexane / 0.5 h / -40 - -20 °C
13.1: tetrahydrofuran / 0.17 h / -78 °C
14.1: NaN(TMS)2 / tetrahydrofuran / 1 h / -78 - -70 °C
14.2: 90 percent / tetrahydrofuran / 1 h / -70 - -60 °C
15.1: 81 percent / n-Bu3SnH; AIBN / toluene / 2 h / Heating
16.1: 95 percent / aq. HCl / methanol / 1 h / 40 °C
17.1: 90 percent / p-TsOH / benzene / 8 h / Heating
18.1: 85 percent / N,N-bis(salicylidene)ethylenediiminocobalt(II); O2 / dimethylformamide / 5 h / 20 °C
With
piperidine; hydrogenchloride; sodium tetrahydroborate; palladium on activated charcoal; lithium aluminium tetrahydride; n-butyllithium; ortho-nitrophenyl selenocyanate; salcomine; Crabtree's catalyst; 2,2'-azobis(isobutyronitrile); tributylphosphine; hydrogen; oxygen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; hydroquinone;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1,2-dichloro-benzene; toluene; benzene;
DOI:10.1021/ol016285h