Multi-step reaction with 16 steps
1: HCl / 5 h / 24 °C
2: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 40 min
3: 81 percent / piperidine / ethanol / 1 h / Heating
4: 75 percent / TiCl4, Et3N / CH2Cl2 / 6.5 h / 0 - 25 °C
5: t-BuOK / benzene / 3 h / 24 °C
6: DDQ / tetrahydrofuran / 1 h / -30 °C
7: 92 percent / Na2CO3 / tetrahydrofuran / 4 h / 25 °C
8: 81 percent / i-Pr2NEt / CHCl3 / 6 h / Heating
9: 42 percent / 4 N aq. LiOH / dimethylsulfoxide / 26 h / 130 - 135 °C
10: 1.) Et3N, diphenyl phosphorazidate, 2.) 4 N aq. LiOH / 1.) benzene, a) 25 deg C, 15 min, b) reflux, 7 h, 2.) 25 deg C, 1 h
11: 80 percent / HgBr(g) / CH2Cl2 / 2 h / 0 °C
12: 69 percent / aq. potassium nitrosulfonate, Bu4NHSO4 / CH2Cl2 / 4 h / 25 °C
13: 1.) Ti(O-i-Pr)4, 2.) NaOMe / 1.) THF, 0 deg C, 45 min, 2.) THF, 0 deg C, 1 h
14: 85 percent / aq. NaN3 / 21 h / 25 °C
15: 86 percent / NaBH4 / tetrahydrofuran; methanol / 1 h / 25 °C
16: TFA, H2, HBr / 10percent Pd/C / 1 h / 80 °C
With
piperidine; titanium(IV) isopropylate; hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; sodium azide; potassium nitrosulfonate; diphenyl phosphoryl azide; potassium tert-butylate; hydrogen bromide; hydrogen; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; mercury(I) bromide; titanium tetrachloride; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; dimethyl sulfoxide; benzene;
DOI:10.1021/ja00076a035