Multi-step reaction with 13 steps
1: 85 percent / LiAl(OEt)2H2 / diethyl ether
2: 87 percent / H2 / 10percent Pd/C / H2O
3: 100 percent / H2O2 / methanol
4: 65 percent / pyridine / CH2Cl2
5: 92 percent / DMAP / acetonitrile
6: 94 percent / aq.LiOH / tetrahydrofuran
7: Dess-Martin periodinane / CH2Cl2
8: NaClO2 / 2-methyl-propan-2-ol
9: 85 percent / tetrahydrofuran
10: 70 percent / catecholborane bromide / CH2Cl2 / 0.25 h / Ambient temperature
11: 87 percent / 1,1'-carbonyldiimidazole / tetrahydrofuran
12: 88 percent / LiSPr-n, HMPA / 2 h / Ambient temperature
13: 50 percent / NaNH2, DABCO / benzene / 0.67 h / 80 °C
With
pyridine; 1,4-diaza-bicyclo[2.2.2]octane; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; sodium chlorite; bromocatecholborane; hydrogen; dihydrogen peroxide; lithium n-propylmercaptide; Dess-Martin periodane; sodium amide; lithium diethoxyaluminum hydride; 1,1'-carbonyldiimidazole;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1021/ja00147a032