Multi-step reaction with 12 steps
1: 95 percent / imidazole / dimethylformamide / 24 °C
2: 75 percent / Swern oxidation
3: 77 percent / tetrahydrofuran / -78 - 0 °C
4: 85 percent / KH / tetrahydrofuran; dimethylformamide / ultrasonication
5: 1) Li, liquid NH3, 2) H2 / 2) 10percent Pd/C / 1) EtOH/THF, -34 degC, 2) AcOEt, r.t.
6: 98 percent / pyridinium chlorochromate / CH2Cl2 / 25 °C
7: 99 percent / KH / tetrahydrofuran / 25 °C
8: 1) BF3*OEt2, 2) diisobutylaluminium hydride / 1) CH2Cl2/hexane, -78 degC, 10 min, 2) -30 degC
9: 90 percent / KH / tetrahydrofuran; dimethylformamide / 23 °C
10: 90 percent / Bu4NF / tetrahydrofuran / 25 °C
11: 94 percent / Bu3P, pyridine / 25 °C
12: 1) m-chloroperbenzoic acid, 2) i-Pr2NEt / 1) CH2Cl2, -42 degC, 2) 190 degC, o-dichlorobenzene
With
pyridine; 1H-imidazole; tributylphosphine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonia; hydrogen; lithium; potassium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)93591-3