Multi-step reaction with 34 steps
1: 69 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 2 h / -78 °C
2: 100 percent / NaBH4 / methanol / 0.25 h / 0 °C
3: 100 percent / imidazole / dimethylformamide / 10 h / 20 °C
4: 99 percent / LiAlH4 / diethyl ether / 0.17 h / 0 °C
5: 94 percent / NaH / dimethylformamide / 12 h / 20 °C
6: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
7: 99 percent / pyridine / 10 h / 20 °C
8: 80 percent / CH3COOH / H2O / 12 h / 65 °C
9: NaIO4; (NH4)2SO4 / methanol; H2O / 0.25 h / 0 °C
10: 13 g / NaBH4 / methanol; H2O / 0.08 h / 0 °C
11: 96 percent / imidazole / dimethylformamide / 5 h / 20 °C
12: 100 percent / K2CO3 / methanol / 2 h / 20 °C
13: 90 percent / pyridinium chlorochromate; molecular sieves 4 Amgstroem / CH2Cl2 / 2 h / 20 °C
14: 86 percent / NaH; 15-crown-5 / toluene / 1 h / 20 °C
15: 97 percent / CH3COOH / H2O / 5 h / 20 °C
16: 100 percent / pyridine / 5 h / 20 °C
17: 90 percent / trimethylsilyl triflate / CH2Cl2 / 18 h / -40 °C
18: 98 percent / NaBH4 / methanol / 0.25 h / 0 °C
19: 93 percent / N-phenylthiosuccinimide; (n-C4H9)3P; pyridine / 6 h / 20 °C
20: 100 percent / K2CO3 / methanol / 3 h / 20 °C
21: (n-C4H9)3P; pyridine / 5 h / 60 °C
22: 16.8 g / Oxone(R) / tetrahydrofuran; methanol; H2O / 3 h / 20 °C
23: (n-C4H9)Li / tetrahydrofuran; hexane / 0.67 h / -30 °C
24: 524 mg / Na; NH3 / tetrahydrofuran / 1 h / -78 °C
25: pyridinium dichromate; molecular sieves 4A / CH2Cl2 / 5 h / 20 °C
26: 3.70 g / C6H5Li / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / 0 °C
27: 85 percent / pyridinium chlorochromate; Al2O3 / benzene / 5 h / 40 °C
28: di(isobutyl)aluminum hydride / toluene; hexane / 0.17 h / -78 °C
29: 80 percent / NaH / tetrahydrofuran / 1 h / 0 °C
30: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
31: 92 percent / (n-C4H9)3P; pyridine / 2 h / 60 °C
32: 90 percent / Oxone(R) / tetrahydrofuran; methanol; H2O / 3 h / 20 °C
33: 98 percent / di(isobutyl)aluminum hydride / toluene; hexane / 0.25 h / -78 °C
34: methanesulfonyl chloride; 4-dimethylaminopyridine / CH2Cl2 / 0.5 h / 20 °C
With
pyridine; 1H-imidazole; dmap; aluminum oxide; ammonium sulfate; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; oxone; diisobutylaluminum hydride; N-(phenylthio)succinimide; 15-crown-5; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; sodium; sodium hydride; potassium carbonate; acetic acid; methanesulfonyl chloride; phenyllithium; pyridinium chlorochromate; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4020(02)01474-6