Multi-step reaction with 10 steps
1: 1.) LDA / 1.) THF, -78 deg C, 2.) r.t., 2h
2: 96 percent / LAH / tetrahydrofuran / 0 °C
3: 96 percent / imidazole / dimethylformamide / -30 °C
4: 1) PCC 2) NaH / 1) CH2Cl2, r.t. 2) THF
5: 1) HF, 2) PCC / 1) acetonitrile, r.t. 2) CH2Cl2, r.t.
6: 1) e-(Hg, SCE), CH2(CO2CH3)2, n-Bu4NBr, 2) LAH / 1) CH3CN 2) THF, 0 deg C
7: 96 percent / imidazole / CH2Cl2 / 0 °C
8: PCC / CH2Cl2 / Ambient temperature
9: 1) NaH / 1) THF, r.t.
With
1H-imidazole; lithium aluminium tetrahydride; hydrogen fluoride; tetrabutylammomium bromide; sodium hydride; pyridinium chlorochromate; malonic acid dimethyl ester; lithium diisopropyl amide;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(90)87014-Q