Multi-step reaction with 21 steps
1: NaIO4 / acetone; H2O / 3 h
2: 90.6 percent / magnesium powder / diethyl ether / 2 h / 27 °C
3: 98 percent / PCC, molecular sieves 3A / CH2Cl2 / 1.5 h / 25 °C
4: 1.) NH2NH2xH2O, Et3N, 2.) I2, 1,1,3,3-tetramethylquanidine / 1.) ethanol, 70 deg C, 1 h, 2.) toluene, 0 deg C, 0.5 h
5: butyllithium / diethyl ether; hexane / 1 h / -100 °C
6: H2, ClRh(PPh3)3 / benzene / 120 h / 24 °C / 36775.4 Torr
7: 95 percent / 46percent aqueous / HF / acetonitrile / 1 h / 24 °C
8: KOH / dimethylformamide / 5 h / 24 °C
9: 93 percent / 2,6-lutidine / CH2Cl2 / 1.5 h / 23 °C
10: 92 percent / H2 / palladium black / ethanol / 0.5 h / 20 °C
11: 82 percent / imidazole / dimethylformamide / 3 h / 25 °C
12: 85 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 3 h / 25 °C
13: 86 percent / 4-dimethylaminopyridine / pyridine / 20 h / 60 °C
14: 81 percent / tetrabutylammonium fluoride / tetrahydrofuran / 8 h / 60 °C
15: 85 percent / pyridinium dichromate, molecular sieves 3A / CH2Cl2 / 4 h / 22 °C
16: 96 percent / aqueous NaOH / dioxane / 2 h / 23 °C
17: 95 percent / triphenylphosphine / tetrahydrofuran / 8 h / 22 °C
18: 65 percent / toluene / 14 h / 110 °C
19: acetic acid / H2O / 4 h / 24 °C
20: 80 percent / 10-campphorsulfonic acid / CH2Cl2 / 24 h / 0 °C
21: 80 percent / pyridinium chlorochromate molecular sieves 3A / CH2Cl2 / 0.5 h / 0 °C
With
1H-imidazole; 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium hydroxide; sodium periodate; Wilkinson's catalyst; dipyridinium dichromate; n-butyllithium; 3 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; iodine; pyridinium p-toluenesulfonate; hydrazine hydrate; magnesium; acetic acid; triethylamine; triphenylphosphine; pyridinium chlorochromate; N,N,N',N'-tetramethylguanidine;
hydrogen fluoride; palladium;
In
tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1246/bcsj.62.2618