Multi-step reaction with 13 steps
1: 87 percent / DIPEA / CH2Cl2 / 5 h / 0 - 20 °C
2: 98 percent / LiAlH4 / diethyl ether / 2 h / 0 - 20 °C
3: 93 percent / N-bromosuccinimide / dimethylformamide / 2 h / 0 °C
4: 95 percent / NaH / dimethylformamide / 1 h / 0 - 20 °C
5: 95 percent / n-BuLi / hexane; diethyl ether / 3 h / -78 - 20 °C
6: 94 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C
7: 72 percent / K2CO3 / acetone / 1 h / 20 °C
8: 90 percent / Cs2CO3 / dimethylformamide / 1 h / 20 °C
9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 3.25 h / -78 - 20 °C
10: 98 percent / Dess-Martin periodinane / CH2Cl2 / 0.75 h / 20 °C
11: 79 percent / H2 / Pd/C / ethanol / 1 h / 20 °C / 760 Torr
12: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
13: aq. NaH2PO4; NaClO2; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol / 1 h / 20 °C
With
hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; 2-methyl-but-2-ene; hydrogen; sodium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
10: Dess-Martin oxidation / 12: Dess-Martin oxidation;
DOI:10.1016/S0040-4020(01)01250-9