Multi-step reaction with 7 steps
1: 87 percent / DMAP / pyridine / 1.) 0 deg C -> 25 deg C, 1 h, 2.) 25 deg C, 48 h
2: 71 percent / LiCl, 4A sieves, Me4Sn, 2,6-di-tert-butylhydroxytoluene / PdCl2(dppf) / dimethylformamide / 12 h / 90 °C / 2585.7 Torr
3: 1.) LiHMDS, 2,2,2-trifluoroethyl trifluoroacetate, 2.) MsN3, Et3N / 1.) THF, -78 deg C, 45 min, 2.) MeCN, H2O, 25 deg C, 6 h
4: 64 percent / benzene / 24 h / Ambient temperature; Irradiation
5: 84 percent / n-Bu4NF, O2 / tetrahydrofuran / 40 h / 25 °C
6: 100 percent / conc. H2SO4 / ethanol / 0.75 h / 25 °C
7: 91 percent / DDQ / benzene / 42 h / 25 °C
With
dmap; 2,2,2-trifluoroethyl trifluoroacetate; 4 A molecular sieve; sulfuric acid; 2,4-di-t-butyl-3-methyl phenol; tetrabutyl ammonium fluoride; oxygen; tetramethylstannane; triethylamine; Methanesulfonyl azide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; lithium hexamethyldisilazane;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
tetrahydrofuran; pyridine; ethanol; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00131a006