Multi-step reaction with 8 steps
1.1: 1,1,1,3,3,3-hexamethyl-disilazane; lithium iodide / dichloromethane / 24 h / 20 °C / Inert atmosphere; Darkness
2.1: diethylzinc / diethyl ether / 18 h / Inert atmosphere; Reflux
3.1: water; sodium hydroxide / ethanol / 12 h / Reflux
4.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere
4.2: 12 h / 20 °C / Inert atmosphere
5.1: N-Bromosuccinimide; sodium acetate / tetrahydrofuran; water / 12 h / 20 °C
6.1: sodium hydrogencarbonate; sodium azide / N,N-dimethyl-formamide / 2 h / 0 °C / Inert atmosphere
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
8.1: sodium cyanoborohydride; acetic acid / methanol / 12 h / 40 °C / Inert atmosphere
With
N-Bromosuccinimide; lithium aluminium tetrahydride; sodium azide; water; diethylzinc; sodium acetate; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane; sodium hydroxide; lithium iodide; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;
2.1: |Simmons-Smith Cyclopropanation;
DOI:10.1016/j.bmc.2013.01.041