Multi-step reaction with 11 steps
1.1: sodium hexamethyldisilazane / 1.5 h / -78 °C / Inert atmosphere
1.2: 6 h / -50 °C
2.1: lithium borohydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
3.1: 1H-imidazole / dichloromethane / 3 h / 20 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C / Inert atmosphere
5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 20 °C / Inert atmosphere
6.1: toluene / 2 h / Inert atmosphere; Reflux
7.1: hydrogenchloride / ethanol / 7 h / 0 °C / Inert atmosphere
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h / 20 °C / Inert atmosphere
9.1: chromium dichloride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
10.1: n-butyllithium; zinc(II) chloride / tetrahydrofuran / 1.25 h / -78 - 20 °C / Inert atmosphere
10.2: 20 °C / Inert atmosphere
11.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere
With
1H-imidazole; chromium dichloride; hydrogenchloride; lithium borohydride; n-butyllithium; sodium hexamethyldisilazane; diisobutylaluminium hydride; zinc(II) chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; toluene;
6.1: |Wittig Olefination / 9.1: |Takai-Utimoto Olefination;
DOI:10.3390/molecules19022213